Anilide derivatives and their use for combating botrytis

ABSTRACT

The use of nicotinic anilide derivatives of the general formula ##STR1## where the substituents have the following meanings: R 1  halogen, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl 
     R 2  unsubstituted or halogen-substituted alkyl, unsubsituted or halogen-substituted alkenyl, alkynyl, unsubstituted or halogen-substituted alkoxy, unsubstituted or halogen-substituted alkenyloxy, alkynyloxy, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkenloxy 
     for combating Botrytis, and nicotinic anilides of the formula I.

The present invention relates to the use of anilide derivatives of thegeneral formula ##STR2## where A has the following meanings:

pyridin-3-yl substituted in the 2-position by halogen, methyl,trifluoromethyl, methoxy, methylthio, methylsulfinyl or methylsulfonyl,

phenyl substituted in 2-position by methyl, trifluoromethyl, chlorine,bromine or iodine,

2-methyl-5,6-dihydropyran-3-yl, 2-methyl-5,6-dihydro-1,4-oxathiin-3-yl,2-methyl-5,6-dihydro-1,4-oxathiin-3-yl-4-oxide,2-methyl-5,6-dihydro-1,4-oxathiin-3-yl-4,4-dioxide; 2-methyl-furan-3-ylsubstituted in the 4- and 5-positions by hydrogen or methyl;thiazol-5-yl substituted in the 2- and 4-positions by hydrogen, methyl,chlorine or trifluoromethyl; thiazol-4-yl substituted in the 2- and5-positions by hydrogen, methyl, chlorine or trifluoromethyl;1-methylpyrazol-4-yl substituted in the 3- and 5-positions by methyl,chlorine or trifluoromethyl; or oxazol-5-yl substituted the 2- and4-positions by hydrogen, methyl or chlorine, and

R has the following meanings: unsubstituted or halogen-substituted C₂-C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃-C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy,unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂-alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆-cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆-cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆-cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆-cycloalkenyloxy, or phenyl which is unsubstituted or substituted by C₁-C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or halogen, for combatingBotrytis.

The present invention further relates to novel anilide derivatives.

It is known to use nicotinic anilides, e.g.,2-chloronicotic-2'-ethylanilide (U.S. Pat. No. 4,001,416) and2-chloronicotic-3'-isopropyl-anilide (DE 26 11 601), as fungicides.

We have now found that the anilide derivatives defined at the outsethave a good action on Botrytis.

In view of their action, those compounds are preferred in which thesubstituents have the following meanings:

halogen, e.g., fluorine, chlorine and bromine,

alkyl, especially ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl,2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl,2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl,2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl,1-ethyl-2-methylpropyl, n-heptyl, 1-methylhexyl, 1-ethylpentyl,2-ethylpentyl, 1-propylbutyl, octyl, decyl or dodecyl, where alkyl maybear from one to three of the abovementioned halogen atoms, especiallyfluorine and chlorine,

alkenyl, such as 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2'-dimethyl-2-propenyl, 1-ethyl-2-propenyl,2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl,2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl,1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl,4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl,3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1'-dimethyl-2-butenyl,1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl,2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl,1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and1-ethyl-2-methyl-2-propenyl, especially 2-propenyl, 2-butenyl,3-methyl-2-butenyl and 3-methyl-2-pentenyl, where alkenyl may bear fromone to three of the abovementioned halogen atoms, especially fluorineand chlorine, alkynyl, such as 2-propynyl, 2-butynyl, 3-butynyl,1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl,1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl,1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2 -hexynyl, 3-hexynyl,4-alkynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,2-dimethyl-2-butynyl,1,1-dimethyl-3-butynyl, 1,2-dimethyl- 3-butynyl,2,2'-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl,2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl, alkoxy, especiallyethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy,2-methylpropoxy, 1,1-dimethylethoxy, n-pentyloxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,2-dimethylpropoxy,1,1-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexyloxy,1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy,4-methylpentyloxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,3-dimethylbutoxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy,3,3-dimethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy,1-ethylbutoxy, 2-ethylbutoxy, 1-ethyl-2-methylpropoxy, n-heptyloxy,1-methylhexyloxy, 2-methylhexyloxy, 3-methylhexyloxy, 4-methylhexyloxy,5-methylhexyloxy, 1-ethylpentyloxy, 2-ethylpentyloxy, 1-propylbutoxy,octyloxy, decyloxy, and dodecyloxy, where alkoxy may bear from one tothree of the above-mentioned halogen atoms, especially fluorine andchlorine, alkenyloxy such as 2-propenyloxy, 2-butenyloxy, 3-butenyloxy,1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-pentenyloxy,3-pentenyloxy, 4-pentenyloxy, 1-methyl-2 -butenyloxy,2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy,2-methyl-3 -butenyloxy, 3-methyl-3-butenyloxy,1,1-dimethyl-2-propenyloxy, 1,2-dimethyl-2-propenyloxy,1-ethyl-2-propenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy,5-hexenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy,3-methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy,2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy,1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy,4-methyl-4 -pentenyloxy, 1,1-dimethyl-2-butenyloxy,1,1-di-methyl-3-butenyloxy, 1,2-dimethyl-2-butenyloxy,1,2-dimethyl-3-butenyloxy, 1,3-dimethyl-2-butenyloxy,1,3-dimethyl-3-butenyloxy, 2,2-dimethyl-3-butenyloxy,2,3-dimethyl-2-butenyloxy, 2,3 -dimethyl-3-butenyloxy, 1-ethyl-2-butenyloxy, 1-ethyl-3-butenyloxy, 2-ethyl-2-butenyloxy,2-ethyl-3-butenyloxy, 1,1,2-trimethyl-2-propenyloxy,1-ethyl-1-methyl-2-propenyloxy and 1-ethyl-2-methyl-2-propenyloxy,especially 2-propenyloxy, 2-butenyloxy, 3-methyl-2-butenyloxy and3-methyl-2-pentenyloxy;

where alkenyloxy may bear from one to three of the above-mentionedhalogen atoms, especially fluorine and chlorine;

alkynyloxy such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy,1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy,1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-methyl-2-butynyloxy,1,1-dimethyl-2-propynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy,3-hexynyloxy, 4-alkynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy,1-methyl-3-pentynyloxy, 1-methyl-4-pentynyloxy, 2 -methyl-3-pentynyloxy,2-methyl-4-pentynyloxy, 3-methyl-4-pentynyloxy, 4-methyl-3-pentynyloxy,1,1-dimethyl-2-butynyloxy, 1,1'-dimethyl-3-butynyloxy,1,2-dimethyl-3-butynyloxy, 2,2-dimethyl-3-butynyloxy,1-ethyl-2-butynyloxy, 1-ethyl-3-butynyloxy, 2-ethyl-3-butynyloxy and1-ethyl-1-methyl-2-propynyloxy, preferably 2-propynyloxy, 2-butynyloxy,1-methyl-2-propynyloxy and 1-methyl-2-butynyloxy,

C₃ -C₆ -cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl andcyclohexyl, where cycloalkyl is unsubstituted or substituted by one tothree C₁ -C₄ -alkyl radicals;

C₄ -C₆ -cycloalkenyl, such as cyclobutenyl, cyclopentenyl andcyclohexenyl, which is unsubstituted or substituted by one to three C₁-C₄ -alkyl radicals;

C₅ -C₆ -cycloalkoxy such as cyclopentyloxy or cyclohexyloxy, which maybe substituted by one to three C₁ -C₄ -alkyl radicals;

C₅ -C₆ -cycloalkenyloxy such as cyclopentyloxy or cyclohexaryloxy, whichmay be substituted by one to three C₁ -C₄ -alkyl radicals.

For combating Botrytis, the use of nicotinic anilide derivatives of theformula I in which the substituents have the meanings given below ispreferred: ##STR3##

R¹ halogen, methyl, trifluoromethyl, methoxy, methylthio,methylsulfinyl, methylsulfonyl

R² unsubstituted or halogen-substituted C₂ -C₁₂ -alkyl, unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted orhalogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, C₃ -C₆-cycloalkyl, C₄ -C₆ -cycloalkenyl, C₅ -C₆ -cycloalkyloxy, C₅ -C₆-cycloalkenyloxy.

The compounds of the formula I are obtained for instance by reacting acorrespondingly substituted nicotinic halide of the formula 2 ##STR4##Hal denoting chlorine or bromine, with an ortho-substituted aniline ofthe formula 3 in the presence of a base. The nicotinic acids and theirhalides of the formula 2 are known. The anilines of the formula 3 areknown or can be prepared by known methods (Helv. Chim. Acta 60, 978(1977); Zh. Org. Khim 26, 1527(1990); Heterocyclus 26, 1885 (1987); Izv.Akad. Nauk. SSSR Ser. Khim 1982, 2160).

Compounds of the formula I in which R¹ is chlorine and R² has themeanings given above are particularly preferred.

                  TABLE 1                                                         ______________________________________                                        Compounds of the formula I                                                     ##STR5##                      I                                                                            Phys. data                                      No.  R.sup.1  R.sup.2         m.p. [°C.]                               ______________________________________                                        1.1  F        n-C.sub.3 H.sub.7                                               1.2  F        i-C.sub.3 H.sub.7                                               1.3  F        sec.-C.sub.4 H.sub.9                                                                           52-54                                          1.4  F        i-C.sub.4 H.sub.9                                                                              87-89                                          1.5  Cl       n-C.sub.3 H.sub.7                                                                             103-104                                         1.6  Cl       n-C.sub.4 H.sub.9                                               1.7  Cl       sec.-C.sub.4 H.sub.9                                                                           94-96                                          1.8  Cl       i-C.sub.4 H.sub.9                                                                              99-101                                         1.9  Cl       tert.-C.sub.4 H.sub.9                                                                         118-120                                         1.10 Cl       n-C.sub.5 H.sub.11                                              1.11 Cl       sec.-C.sub.5 H.sub.11                                           1.12 Cl       n-C.sub.6 H.sub.13                                              1.13 Cl       n-C.sub.7 H.sub.15                                              1.14 Cl       sec.-C.sub.7 H.sub.15                                           1.15 Cl       n-C.sub.8 H.sub.17                                              1.16 Cl       n-C.sub.10 H.sub.23                                             1.17 Cl       n-C.sub.12 H.sub.25                                             1.18 Cl       1-Methylvinyl    90-91                                          1.19 Cl       2-Methylvinyl                                                   1.20 Cl       Allyl                                                           1.21 Cl       2-Methylallyl                                                   1.22 Cl       2-Ethylallyl                                                    1.23 Cl       1-Methylallyl                                                   1.24 Cl       1-Ethylallyl                                                    1.25 Cl       1-Methyl-2-butenyl                                              1.26 Cl       1-Ethyl-2-butenyl                                               1.27 Cl       1-Isopropyl-2-butenyl                                           1.28 Cl       1-n-Butyl-2-butenyl                                             1.29 Cl       1-Methyl-2-pentenyl                                             1.30 Cl       1,4-Dimethyl-2-pentenyl                                         1.31 Cl       Propargyl                                                       1.32 Cl       2-Butynyl                                                       1.33 Cl       3-Butynyl                                                       1.34 Cl       Ethoxy          131-132                                         1.35 Cl       Propoxy                                                         1.36 Cl       1-Methylethoxy   65-67                                          1.37 Cl       n-Butoxy         84-85                                          1.38 Cl       1-Methylpropoxy  72-74                                          1.39 Cl       2-Methylpropoxy  81-84                                          1.40 Cl       1,1-Dimethylethoxy                                              1.41 Cl       n-Pentyloxy                                                     1.42 Cl       n-Hexyloxy                                                      1.43 Cl       n-Hepyloxy                                                      1.44 Cl       n-Octyloxy                                                      1.45 Cl       2-Ethylhexyloxy                                                 1.46 Cl       n-Decyloxy                                                      1.47 Cl       2-Propenyloxy    86-88                                          1.48 Cl       2-Butentyloxy    92-95                                          1.49 Cl       2-Methyl-2-propenyloxy                                                                         75-76                                          1.50 Cl       2-Pentenyloxy                                                   1.51 Cl       3-Pentenyloxy                                                   1.52 Cl       3-chloro-2-propenyloxy                                          1.53 Cl       2,3-Dichloro-2-                                                               propenyloxy                                                     1.54 Cl       2,3,3-Trichloro-                                                              propenyloxy                                                     1.55 Cl       2-Propynyloxy    79-84                                          1.56 Cl       2-Butynyl-oxy                                                   1.57 Cl       3-Butynyl-oxy                                                   1.58 Cl       1-Methyl-2-propynyloxy                                          1.59 Cl       Cyclopropyl     144-145                                         1.60 Cl       Cyclobutyl                                                      1.61 Cl       Cyclopentyl     112-114                                         1.62 Cl       Cyclohexyl      141-142                                         1.63 Cl       2-Cyclopentenyl 123-124                                         1.64 Cl       1-Cyclopentenyl                                                 1.65 Cl       2-Cyclohexenyl   92-93                                          1.66 Cl       1-Cyclohexenyl                                                  1.67 Cl       Cyclopentyloxy   80-82                                          1.68 Cl       Cyclohexyloxy                                                   1.69 Cl       2-Cyclopentenyloxy                                              1.70 Cl       2-Cyclohexenyloxy                                                                             oil                                             1.71 Br       sec.-Butyl                                                      1.72 Br       i-Butyl                                                         1.73 CH.sub.3 sec.-Butyl                                                      1.74 CH.sub.3 i-Butyl                                                         1.75 CF.sub.3 i-Propyl                                                        1.76 CF.sub.3 sec.-Butyl                                                      1.77 CF.sub.3 i-Butyl                                                         1.78 OCH.sub.3                                                                              i-Propyl                                                        1.79 OCH.sub.3                                                                              sec.-Butyl      oil NMR 0.8t(3H);                                                             1.2d(3H); 1.6m(2H);                                                           3.0q(1H); 4.1s(3H);                                                           7.2m(3H); 7.3m(1H);                                                           8.3m(1H); 8.4m(1H),                                                           9.8s(1H)                                        1.80 OCH.sub.3                                                                              i-Butyl         oil NMR 0,8d(6H);                                                             1.9m(1H); 2.5d(2H),                                                           4.05s(3H), 7.2m(4H);                                                          7.8d(1H); 8.3d(1H);                                                           8.4m(1H); 9.8s(1H)                              1.81 SCH.sub.3                                                                              i-Propyl                                                        1.82 SCH.sub.3                                                                              sec.-Butyl       89-91                                          1.83 SCH.sub.3                                                                              i-Butyl         140-141                                         1.84 SO.sub.2 CH.sub.3                                                                      sec.-Butyl      191-192                                         1.85 SO.sub.2 CH.sub.3                                                                      i-Butyl         150-153                                         1.86 Cl       2-Ethylpropoxy   65-66                                          1.87 Cl       3-Methyl-3-butenyloxy                                                                          83-84                                          ______________________________________                                    

MANUFACTURING EXAMPLES EXAMPLE 1

At 0° C., 3.5 g of 2-chloroonicotic chloride is dripped into a solutionof 2.7 g of 2-n-propylaniline and 2.0 g of triethylamine in 30 mloftetrahydrofuran, and the mixture is stirred for 2 hours at 0° C. Afterdilution with 300 ml of water, there is isolated 3.2 g of2-chloronicotic acid-2-n-propylanilide; m.p.: 103°-104° C. (No. 1.5).

EXAMPLE 2

4.4 g of 2-chloroonicotic acid-2-sec.-butylanilide (Table 1, No. 7) isrefluxed for 2 hours in a solution of 5.5 g of 30% strength sodiummethylate solution in 20 ml of methanol. After dilution with 250 ml ofwater the mixture is extracted twice, each time with 100 ml of ethylacetate. From the combined organic phases there is isolated, afterdrying and evaporation of the solvent, 3.8 g of 2-methoxy-nicotinicacid-2-sec.-butylanilide as an oil (No. 1.79).

EXAMPLE 3

Similarly to Example 1, there is obtained from 5.7 g of2-methylthionicoticchloroide, 4.6 g of 2-sec-butylaniline and 3.1 g oftriethylamine 6.6 g of 2-methylthionicotic acid-2-sec.-butylanilide;m.p.: 89°14 91° C. (No. 1.82).

EXAMPLE 4

While stirring at 35° C., 2.20 g of 30% strength hydrogen peroxyde isdripped into a mixture of 2.00 g of the abovementioned product(Example3) in 5 ml of glacial acetic acid and 0.13 g of sodiumtungstate, and the mixture is stirred for 3 hours at 35° C. Afterdilution with 15 ml of water, removal of the crystals by suctionfiltration, washing with water and drying, there is obtained 1.7 g of2-methylsulfonylnicotic acid-2-sec.-butylanilide; m.p.: 191°-192° C.(No. 1.84).

The invention further relates to the use of anilide derivatives of theformula II ##STR6##where the substituents have the following meanings:##STR7##

X methylene or sulfur

R unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted orhalogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy,unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl,unsubstituted orC₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl,unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy,unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy

for combating Botrytis.

The compounds of the formula 2 are obtained for instance by reacting acorrespondingly substituted carboxylic halide of the formula 4 with anortho-substituted aniline of the formula 3 in the presence of a base:##STR8##

Hal is chlorine or bromine.

The carboxylic acids and their halides ACO₂ H and A--Co--Hal (4) areknown.

                  TABLE 2                                                         ______________________________________                                        Compounds of the formula II                                                    ##STR9##                                                                                                         Phys. data                                No.    A     R                 X    mp [°C.]                           ______________________________________                                        2.1    A.sub.1                                                                             i-C.sub.3 H.sub.7 --   108-109                                   2.2    A.sub.1                                                                             n-C.sub.3 H.sub.7 --   112-114                                   2.3    A.sub.1                                                                             n-C.sub.4 H.sub.9 --                                             2.4    A.sub.1                                                                             sec.-C.sub.4 H.sub.9                                                                            --   89-90                                     2.5    A.sub.1                                                                             i-C.sub.4 H.sub.9 --   118-119                                   2.6    A.sub.1                                                                             tert.-C.sub.4 H.sub.9                                                                           --                                             2.7    A.sub.1                                                                             n-C.sub.5 H.sub.11                                                                              --                                             2.8    A.sub.1                                                                             sec.-C.sub.5 H.sub.11                                                                           --                                             2.9    A.sub.1                                                                             n-C.sub.6 H.sub.13                                                                              --                                             2.10   A.sub.1                                                                             n-C.sub.7 H.sub.15                                                                              --                                             2.11   A.sub.1                                                                             sec.-C.sub.7 H.sub.15                                                                           --                                             2.12   A.sub.1                                                                             1-Methylvinyl     --                                             2.13   A.sub.1                                                                             2-Methylvinyl     --                                             2.14   A.sub.1                                                                             Allyl             --                                             2.15   A.sub.1                                                                             2-Methylallyl     --                                             2.16   A.sub.1                                                                             2-Ethylallyl      --                                             2.17   A.sub.1                                                                             1-Methylallyl     --                                             2.18   A.sub.1                                                                             1-Ethylallyl      --                                             2.19   A.sub. 1                                                                            1-Methyl-2-butenyl                                                                              --                                             2.20   A.sub.1                                                                             1-Ethyl-2-butenyl --                                             2.21   A.sub.1                                                                             1-Isopropyl-2-butenyl                                                                           --                                             2.22   A.sub.1                                                                             1-n-Butyl-2-butenyl                                                                             --                                             2.23   A.sub.1                                                                             1-Methyl-2-pentenyl                                                                             --                                             2.24   A.sub.1                                                                             1,4-Dimethyl-2-pentenyl                                                                         --                                             2.25   A.sub.1                                                                             Propargyl         --                                             2.26   A.sub.1                                                                             2-Butynyl         --                                             2.27   A.sub.1                                                                             3-Butynyl         --                                             2.28   A.sub.1                                                                             Ethoxy            --                                             2.29   A.sub.1                                                                             Propoxy           --                                             2.30   A.sub.1                                                                             1-Methylethoxy    --                                             2.31   A.sub.1                                                                             n-Butoxy          --                                             2.32   A.sub.1                                                                             1-Methylpropoxy   --   46-84                                     2.33   A.sub.1                                                                             2-Methylpropoxy   --                                             2.34   A.sub.1                                                                             1,1-Dimethylethoxy                                                                              --                                             2.35   A.sub.1                                                                             n-Pentyloxy       --                                             2.36   A.sub.1                                                                             n-Hexyloxy        --                                             2.37   A.sub.1                                                                             2-Ethylhexyloxy   --                                             2.38   A.sub.1                                                                             2-Propenyloxy     --                                             2.39   A.sub.1                                                                             2-Butentyloxy     --   62-66                                     2.40   A.sub.1                                                                             2-Methyl-2-propenyloxy                                                                          --   oil                                       2.41   A.sub.1                                                                             2-Pentenyloxy     --                                             2.42   A.sub.1                                                                             3-Pentenyloxy     --                                             2.43   A.sub.1                                                                             3-chloro-2-propenyloxy                                                                          --                                             2.44   A.sub.1                                                                             2,3-Dichloro-2-propenyloxy                                                                      --                                             2.45   A.sub.1                                                                             2,3,3-Trichloro-propenyloxy                                                                     --                                             2.46   A.sub.1                                                                             2-Propynyloxy     --                                             2.47   A.sub.1                                                                             2-Butynyl-oxy     --                                             2.48   A.sub.1                                                                             3-Butynyl-oxy     --                                             2.49   A.sub.1                                                                             1-Methyl-2-propynyloxy                                                                          --                                             2.50   A.sub.1                                                                             Cyclopropyl       --                                             2.51   A.sub.1                                                                             Cyclobutyl        --                                             2.52   A.sub.1                                                                             Cyclopentyl       --   112-113                                   2.53   A.sub.1                                                                             Cyclohexyl        --   120-121                                   2.54   A.sub.1                                                                             2-Cyclopentenyl   --   128-129                                   2.55   A.sub.1                                                                             1-Cyclopentenyl   --                                             2.56   A.sub.1                                                                             2-Cyclohexenyl    --   95-96                                     2.57   A.sub.1                                                                             1-Cyclohexenyl    --                                             2.58   A.sub.1                                                                             Cyclopentyloxy    --                                             2.59   A.sub.1                                                                             Cyclohexyloxy     --                                             2.60   A.sub.1                                                                             2-Cyclopentenyloxy                                                                              --                                             2.61   A.sub.1                                                                             2-Cyclohexenyloxy --   oil                                       2.62   A.sub.2                                                                             i-C.sub.3 H.sub.7 CH.sub.2                                                                            99-101                                   2.63   A.sub.2                                                                             n-C.sub.3 H.sub.7 CH.sub.2                                       2.64   A.sub.2                                                                             n-C.sub.4 H.sub.9 CH.sub.2                                       2.65   A.sub.2                                                                             sec.-C.sub.4 H.sub.9                                                                            CH.sub.2                                                                           81-82                                     2.66   A.sub.2                                                                             i-C.sub.4 H.sub.9 CH.sub.2                                                                           81-83                                     2.67   A.sub.2                                                                             tert.-C.sub.4 H.sub.9                                                                           CH.sub.2                                       2.68   A.sub.2                                                                             n-C.sub.5 H.sub.11                                                                              CH.sub.2                                       2.69   A.sub.2                                                                             sec.-C.sub.5 H.sub.11                                                                           CH.sub.2                                       2.70   A.sub.2                                                                             n-C.sub.6 H.sub.13                                                                              CH.sub.2                                       2.71   A.sub.2                                                                             n-C.sub.7 H.sub.15                                                                              CH.sub.2                                       2.72   A.sub.2                                                                             sec.-C.sub.7 H.sub.15                                                                           CH.sub.2                                       2.73   A.sub.2                                                                             1-Methylvinyl     CH.sub.2                                       2.74   A.sub.2                                                                             2-Methylvinyl     CH.sub.2                                       2.75   A.sub.2                                                                             Allyl             CH.sub.2                                       2.76   A.sub.2                                                                             2-Methylallyl     CH.sub.2                                       2.77   A.sub.2                                                                             2-Ethylallyl      CH.sub.2                                       2.78   A.sub.2                                                                             1-Methylallyl     CH.sub.2                                       2.79   A.sub.2                                                                             1-Ethylallyl      CH.sub.2                                       2.80   A.sub.2                                                                             1-Methyl-2-butenyl                                                                              CH.sub.2                                       2.81   A.sub.2                                                                             1-Ethyl-2-butenyl CH.sub.2                                       2.82   A.sub.2                                                                             1-Isopropyl-2-butenyl                                                                           CH.sub.2                                       2.83   A.sub.2                                                                             1-n-Butyl-2-butenyl                                                                             CH.sub.2                                       2.84   A.sub.2                                                                             1-Methyl-2-pentenyl                                                                             CH.sub.2                                       2.85   A.sub.2                                                                             1,4-Dimethyl-2-pentenyl                                                                         CH.sub.2                                       2.86   A.sub.2                                                                             Propargyl         CH.sub.2                                       2.87   A.sub.2                                                                             2-Butynyl         CH.sub.2                                       2.88   A.sub.2                                                                             3-Butynyl         CH.sub.2                                       2.89   A.sub.2                                                                             Ethoxy            CH.sub.2                                       2.90   A.sub.2                                                                             Propoxy           CH.sub.2                                       2.91   A.sub.2                                                                             1-Methylethoxy    CH.sub.2                                       2.92   A.sub.2                                                                             n-Butoxy          CH.sub.2                                       2.93   A.sub.2                                                                             1-Methylpropoxy   CH.sub.2                                       2.94   A.sub.2                                                                             2-Methylpropoxy   CH.sub.2                                       2.95   A.sub.2                                                                             1,1-Dimethylethoxy                                                                              CH.sub.2                                       2.96   A.sub.2                                                                             n-Pentyloxy       CH.sub.2                                       2.97   A.sub.2                                                                             n-Hexyloxy        CH.sub.2                                       2.98   A.sub.2                                                                             2-Ethylhexyloxy   CH.sub.2                                       2.99   A.sub.2                                                                             2-Propenyloxy     CH.sub.2                                       2.100  A.sub.2                                                                             2-Butentyloxy     CH.sub.2                                       2.101  A.sub.2                                                                             1-Methyl-2-propenyloxy                                                                          CH.sub.2                                                                           67-69                                     2.102  A.sub.2                                                                             2-Pentenyloxy     CH.sub.2                                       2.103  A.sub.2                                                                             3-Pentenyloxy     CH.sub.2                                       2.104  A.sub.2                                                                             3-chloro-2-propenyloxy                                                                          CH.sub.2                                       2.105  A.sub.2                                                                             2,3-Dichloro-2-propenyloxy                                                                      CH.sub.2                                       2.106  A.sub.2                                                                             2,3,3-Trichloro-propenyloxy                                                                     CH.sub.2                                       2.107  A.sub.2                                                                             2-Propynyloxy     CH.sub.2                                       2.108  A.sub.2                                                                             2-Butynyl-oxy     CH.sub.2                                       2.109  A.sub.2                                                                             3-Butynyl-oxy     CH.sub.2                                       2.110  A.sub.2                                                                             1-Methyl-2-propynyloxy                                                                          CH.sub.2                                       2.111  A.sub.2                                                                             Cyclopropyl       CH.sub.2                                       2.112  A.sub.2                                                                             Cyclobutyl        CH.sub.2                                       2.113  A.sub.2                                                                             Cyclopentyl       CH.sub.2                                                                           109-111                                   2.114  A.sub.2                                                                             Cyclohexyl        CH.sub.2                                                                           118-123                                   2.115  A.sub.2                                                                             2-Cyclopentenyl   CH.sub.2                                                                           87-89                                     2.116  A.sub.2                                                                             1-Cyclopentenyl   CH.sub.2                                       2.117  A.sub.2                                                                             2-Cyclohexenyl    CH.sub.2                                                                           85-87                                     2.118  A.sub.2                                                                             1-Cyclohexenyl    CH.sub.2                                       2.119  A.sub.2                                                                             Cyclopentyloxy    CH.sub.2                                                                           60-91                                     2.120  A.sub.2                                                                             Cyclohexyloxy     CH.sub.2                                       2.121  A.sub.2                                                                             2-Cyclopentenyloxy                                                                              CH.sub.2                                       2.122  A.sub.2                                                                             2-Cyclohexenyloxy CH.sub.2                                                                           oil                                       2.123  A.sub.2                                                                             i-C.sub.3 H.sub.7 S                                              2.124  A.sub.2                                                                             n-C.sub.3 H.sub.7 S                                              2.125  A.sub.2                                                                             n-C.sub.4 H.sub.9 S                                              2.126  A.sub.2                                                                             sec.-C.sub.4 H.sub.9                                                                            S    oil                                       2.127  A.sub.2                                                                             i-C.sub.4 H.sub.9 S    oil                                       2.128  A.sub.2                                                                             tert.-C.sub.4 H.sub.9                                                                           S                                              2.129  A.sub.2                                                                             n-C.sub.5 H.sub.11                                                                              S                                              2.130  A.sub.2                                                                             sec.-C.sub.5 H.sub.11                                                                           S                                              2.131  A.sub.2                                                                             n-C.sub.6 H.sub.13                                                                              S                                              2.132  A.sub.2                                                                             n-C.sub.7 H.sub.15                                                                              S                                              2.133  A.sub.2                                                                             sec.-C.sub.7 H.sub.15                                                                           S                                              2.134  A.sub.2                                                                             1-Methylvinyl     S                                              2.135  A.sub.2                                                                             2-Methylvinyl     S                                              2.136  A.sub.2                                                                             Allyl             S                                              2.137  A.sub.2                                                                             2-Methylallyl     S                                              2.138  A.sub.2                                                                             2-Ethylallyl      S                                              2.139  A.sub.2                                                                             1-Methylallyl     S                                              2.140  A.sub.2                                                                             1-Ethylallyl      S                                              2.141  A.sub.2                                                                             1-Methyl-2-butenyl                                                                              S                                              2.142  A.sub.2                                                                             1-Ethyl-2-butenyl S                                              2.143  A.sub.2                                                                             1-Isopropyl-2-butenyl                                                                           S                                              2.144  A.sub.2                                                                             1-n-Butyl-2-butenyl                                                                             S                                              2.145  A.sub.2                                                                             1-Methyl-2-pentenyl                                                                             S                                              2.146  A.sub.2                                                                             1,4-Dimethyl-2-pentenyl                                                                         S                                              2.147  A.sub.2                                                                             Propargyl         S                                              2.148  A.sub.2                                                                             2-Butynyl         S                                              2.149  A.sub.2                                                                             3-Butynyl         S                                              2.150  A.sub.2                                                                             Ethoxy            S                                              2.151  A.sub.2                                                                             Propoxy           S                                              2.152  A.sub.2                                                                             1-Methylethoxy    S                                              2.153  A.sub.2                                                                             n-Butoxy          S                                              2.154  A.sub.2                                                                             1-Methylpropoxy   S    oil                                       2.155  A.sub.2                                                                             2-Methylpropoxy   S                                              2.156  A.sub.2                                                                             1,1-Dimethylethoxy                                                                              S                                              2.157  A.sub.2                                                                             n-Pentyloxy       S                                              2.158  A.sub.2                                                                             n-Hexyloxy        S                                              2.159  A.sub.2                                                                             2-Ethylhexyloxy   S                                              2.160  A.sub.2                                                                             2-Propenyloxy     S                                              2.161  A.sub.2                                                                             2-Butentyloxy     S                                              2.162  A.sub.2                                                                             1-Methyl-2-propenyloxy                                                                          S    65-67                                     2.163  A.sub.2                                                                             2-Pentenyloxy     S                                              2.164  A.sub.2                                                                             3-Pentenyloxy     S                                              2.165  A.sub.2                                                                             3-chloro-2-propenyloxy                                                                          S                                              2.166  A.sub.2                                                                             2,3-Dichloro-2-propenyloxy                                                                      S                                              2.167  A.sub.2                                                                             2,3,3-Trichloro-propenyloxy                                                                     S                                              2.168  A.sub.2                                                                             2-Propynyloxy     S                                              2.169  A.sub.2                                                                             2-Butynyl-oxy     S                                              2.170  A.sub.2                                                                             3-Butynyl-oxy     S                                              2.171  A.sub.2                                                                             1-Methyl-2-propynyloxy                                                                          S                                              2.172  A.sub.2                                                                             Cyclopropyl       S                                              2.173  A.sub.2                                                                             Cyclobutyl        S                                              2.174  A.sub.2                                                                             Cyclopentyl       S    62-64                                     2.175  A.sub.2                                                                             Cyclohexyl        S    120-122                                   2.176  A.sub.2                                                                             2-Cyclopentenyl   S    76-78                                     2.177  A.sub.2                                                                             1-Cyclopentenyl   S                                              2.178  A.sub.2                                                                             2-Cyclohexenyl    S    70-72                                     2.179  A.sub.2                                                                             1-Cyclohexenyl    S                                              2.180  A.sub.2                                                                             Cyclopentyloxy    S    88-90                                     2.181  A.sub.2                                                                             Cyclohexyloxy     S                                              2.182  A.sub.2                                                                             2-Cyclopentenyloxy                                                                              S                                              2.183  A.sub.2                                                                             2-Cyclohexenyloxy S    oil                                       2.184  A.sub.1                                                                             1-Ethylpropoxy    --   65-66                                     2.185  A.sub.1                                                                             3-Methyl-2-butenyloxy                                                                           --   oil                                       2.186  A.sub.2                                                                             1-Ethylpropoxy    CH.sub.2                                                                           oil                                       2.187  A.sub.2                                                                             1-Ethylpropoxy    S    oil                                       ______________________________________                                    

Manufacturing examples EXAMPLE 5

At 0° C. 3.1 g of 2-methylbenzoic chloride is dripped into a solution of3.0 g of sec-butyl-aniline and 2.0 g of triethylamine in 30 mloftetrahydrofuran, and the mixture is stirred for 2 hours at 0° C. Afterdilution with 500 ml of water, extraction with ethyl acetate andevaporation of the solvent, there is isolated 2-methylbenzoicacid-2-sec-butylanilide; m.p. 89°-90° C. (Compound No. 2.4).

EXAMPLE 6

At 0° C., 2.5 g thionyl chloride is dripped into a solution of 3.0 gof2-methyl-5,6-dihydropyran-3-carboxylic acid. After the mixture has beenstirred for 1 hour, 2.8 g of 2-isopropylaniline is added and the wholeis stirred for 12 hours at room temperature (20° C.). The pyridine isevaporated off, 50 ml of water is stirred in, the pH is adjusted to 3withdilute hydrochloric acid, and extraction is carried out with ethylacetate.The solvent is evaporated, the residue is mixed with diisopropylether, andthere is isolated 3.3 g of2-methyl-5,6-dihydropyran-3-carboxylic acid-2-isopropylanilide; m.p.;99°-101° C. (Compound No. 2.62).

The invention further relates to the use of 2-aminobiphenyl derivativesof the general formula II ##STR10##where the substituents have thefollowing meanings: ##STR11##

X methylene, sulfur, sulfinyl, sulfonyl (SO₂),

R¹ methyl, trifluoromethly, chlorine, bromine, iodine,

R² trifluoromethyl, chlorine,

R³ hydrogen or methyl

R⁴ methyl, trifluoromethyl, chlorine

R⁵ hydrogen, methyl, chlorine

R⁶ methyl, trifluoromethyl

R⁷ methyl, chlorine

R⁸ C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄-alkylthio, halogen forcombating Botrytis.

The compounds of the formula III are obtained for instance by reacting acorrespondingly substituted carboxylic halide of the formula 4 ##STR12##

Hal denoting chlorine or bromine, with an ortho-substituted aniline ofthe formula 5 in the presence of a base. The carboxylic acids and theirhalides of the formula 4 are known. Some of the anilines of the formula5 are known or can be prepared by known processes (Tetrahedron Letters,Vol.28 p. 5093 (1987); THL Vol 295463 (1988).

                                      TABLE 3                                     __________________________________________________________________________    No.                                                                              A R.sup.1                                                                          R.sup.2                                                                         R.sup.3                                                                          R.sup.4                                                                          R.sup.5                                                                          R.sup.6                                                                          R.sup.7                                                                         R.sup.8                                                                            X  Phys. data [°C.]                       __________________________________________________________________________    3.1                                                                              A.sub.1                                                                         CH.sub.3                                                                         --                                                                              -- -- -- -- --                                                                              2-F  --                                               3.2                                                                              A.sub.1                                                                         CH.sub.3                                                                         --                                                                              -- -- -- -- --                                                                              4-F  --                                               3.3                                                                              A.sub.1                                                                         CF.sub.3                                                                         --                                                                              -- -- -- -- --                                                                              2-F  --                                               3.4                                                                              A.sub.1                                                                         CF.sub.3                                                                         --                                                                              -- -- -- -- --                                                                              4-F  --                                               3.5                                                                              A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              2-F  --                                               3.6                                                                              A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              2-CH.sub.3                                                                         -- 71-73                                         3.7                                                                              A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              2-Cl --                                               3.8                                                                              A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              2-OCH.sub.3                                                                        --                                               3.9                                                                              A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              3-F  --                                               3.10                                                                             A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              3-Cl -- 95-98                                         3.11                                                                             A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              3-CH.sub.3                                                                         --                                               3.12                                                                             A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              3-OCH.sub.3                                                                        --                                               3.13                                                                             A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              3-OiC.sub.3 H.sub.7                                                                --                                               3.14                                                                             A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              3-Br --                                               3.15                                                                             A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              4-F  -- 156-157                                       3.16                                                                             A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              4-Cl --                                               3.17                                                                             A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              4-CH.sub.3                                                                         --                                               3.18                                                                             A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              4-OCH.sub.3                                                                        --                                               3.19                                                                             A.sub.2                                                                         -- Cl                                                                              -- -- -- -- --                                                                              4-SCH.sub.3                                                                        --                                               3.20                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              2-F  CH.sub.2                                         3.21                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              3-F  CH.sub.2                                         3.22                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              4-F  CH.sub.2                                         3.23                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              3-Cl CH.sub.2                                         3.24                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              3-CH.sub.3                                                                         CH.sub.2                                         3.25                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              2-F  S                                                3.26                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              3-F  S                                                3.27                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              4-F  S                                                3.28                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              3-Cl S                                                3.29                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              3-CH.sub.3                                                                         S                                                3.30                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              2-F  SO.sub.2                                         3.31                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              3-F  SO.sub.2                                         3.32                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              4-F  SO.sub.2                                         3.33                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              3-Cl SO.sub.2                                         3.34                                                                             A.sub.3                                                                         -- --                                                                              -- -- -- -- --                                                                              3-CH.sub.3                                                                         SO.sub.2                                         3.35                                                                             A.sub.5                                                                         -- --                                                                              -- CF.sub.3                                                                         CH.sub.3                                                                         -- --                                                                              2-F  --                                               3.36                                                                             A.sub.5                                                                         -- --                                                                              -- CF.sub.3                                                                         CH.sub.3                                                                         -- --                                                                              3-F  --                                               3.37                                                                             A.sub.5                                                                         -- --                                                                              -- CF.sub.3                                                                         CH.sub.3                                                                         -- --                                                                              4-F  --                                               3.38                                                                             A.sub.7                                                                         -- --                                                                              -- -- -- CH.sub.3                                                                         Cl                                                                              2-F  --                                               3.39                                                                             A.sub.7                                                                         -- --                                                                              -- -- -- CH.sub.3                                                                         Cl                                                                              3-F  --                                               3.40                                                                             A.sub.7                                                                         -- --                                                                              -- -- -- CH.sub.3                                                                         Cl                                                                              4-F  --                                               3.41                                                                             A.sub.7                                                                         -- --                                                                              -- -- -- CF.sub.3                                                                         Cl                                                                              2-F  --                                               3.42                                                                             A.sub.7                                                                         -- --                                                                              -- -- -- CF.sub.3                                                                         Cl                                                                              4-F  --                                               __________________________________________________________________________

The invention further relates to the use of 2-aminobiphenyl derivativesof the general formula IV ##STR13##where the substituents have thefollowing meanings: ##STR14##

X methylene, sulfinyl, sulfonyl (SO₂),

R¹ methyl, trifluoromethyl, chlorine, bromine, iodine,

R² trifluoromethyl, chlorine

R³ hydrogen or methyl

R⁴ methyl, trifluoromethyl, chlorine

R⁵ hydrogen, methyl, chlorine

R⁶ methyl, trifluoromethyl

R⁷ methyl, chlorine,

for combating Botrytis.

The compounds of the formula IV are obtained for example by reacting acorresponding aromatic or heterocyclic acid halide 4 with2-aminobiphenyl 6 in the presence of a base. ##STR15##

Hal is chlorine or bromine.

The acids of the formula A--CO₂ H and their halides II are known.

                  TABLE 4                                                         ______________________________________                                         ##STR16##                                                                                                                      Phys.                       No.  A     R.sup.1                                                                              R.sup.2                                                                           R.sup.3                                                                            R.sup.4                                                                            R.sup.5                                                                            R.sup.6                                                                           R.sup.7                                                                           X    data [°C.]           ______________________________________                                        4.1  A.sub.1                                                                             CH.sub.3                                                                             --  --   --   --   --  --  --   87-88                       4.2  A.sub.1                                                                             Br     --  --   --   --   --  --  --   113-115                     4.3  A.sub.2                                                                             --     Cl  --   --   --   --  --  --   151-152                     4.4  A.sub.3                                                                             --     --  --   --   --   --  --  CH.sub.2                                                                           76-77                       4.5  A.sub.4                                                                             --     --  CH.sub.3                                                                           --   --   --  --  --   104-106                     4.6  A.sub.5                                                                             --     --  --   CH.sub.3                                                                           CH.sub.3                                                                           --  --  --   136-137                     ______________________________________                                    

                                      TABLE 5                                     __________________________________________________________________________    No.                                                                              A  R.sup.1                                                                          R.sup.2                                                                          R.sup.3                                                                         R.sup.4                                                                          R.sup.5                                                                          R.sup.6                                                                          R.sup.7                                                                          X  Phys. data [°C.]                          __________________________________________________________________________    5.1                                                                              A.sub.1                                                                          CF.sub.3                                                                         -- --                                                                              -- -- -- -- -- 138-139                                          5.2                                                                              A.sub.1                                                                          J  -- --                                                                              -- -- -- -- -- 129-132                                          5.3                                                                              A.sub.2                                                                          -- CF.sub.3                                                                         --                                                                              -- -- -- -- --                                                  5.4                                                                              A.sub.3                                                                          -- -- --                                                                              -- -- -- -- SO                                                  5.5                                                                              A.sub.3                                                                          -- -- --                                                                              -- -- -- -- SO.sub.2                                            5.6                                                                              A.sub.5                                                                          -- -- --                                                                              CF.sub.3                                                                         CH.sub.3                                                                         -- -- -- 116-118                                          5.7                                                                              A.sub.6                                                                          -- -- --                                                                              CH.sub.3                                                                         CH.sub.3                                                                         -- -- --                                                  5.8                                                                              A.sub.6                                                                          -- -- --                                                                              Cl Cl -- -- --                                                  5.9                                                                              A.sub.7                                                                          -- -- --                                                                              -- -- CH.sub.3                                                                         Cl -- 108-109                                          5.10                                                                             A.sub.7                                                                          -- -- --                                                                              -- -- CF.sub.3                                                                         Cl --                                                  5.11                                                                             A.sub.7                                                                          -- -- --                                                                              -- -- CH.sub.3                                                                         CH.sub.3                                                                         --                                                  5.11                                                                             A.sub.1                                                                          Cl -- --                                                                              -- -- --    -- 100-103                                          __________________________________________________________________________

The invention further relates to the use of carboxanilide derivatives ofthe general formula V ##STR17##where the substituents have the followingmeanings: ##STR18##

n 1 or 2

R¹ trifluoromethyl, chlorine, bromine, iodine,

R² hydrogen or methyl

R³ methyl, trifluoromethyl, chlorine

R⁴ hydrogen, methyl, chlorine,

R^(s) methyl, trifluoromethyl

R⁶ methyl, chlorine

R⁷ unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted orhalogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy,unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl,unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy,unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy

for combating Botrytis.

                  TABLE 6                                                         ______________________________________                                        Compounds of the formula I where A is A.sub.1                                  ##STR19##                                                                                                      Phys. data                                  No.    R.sup.1 R.sup.7            mp [°C.]                             ______________________________________                                        6.1    CF.sub.3                                                                              i-C.sub.3 H.sub.7  160-162                                     6.2    CF.sub.3                                                                              n-C.sub.3 H.sub.7  151-152                                     6.3    CF.sub.3                                                                              n-C.sub.4 H.sub.9                                              6.4    CF.sub.3                                                                              sec.-C.sub.4 H.sub.9                                                                             83-84                                       6.5    CF.sub.3                                                                              i-C.sub.4 H.sub.9  133-135                                     6.6    CF.sub.3                                                                              tert.-C.sub.4 H.sub.9                                          6.7    CF.sub.3                                                                              n-C.sub.5 H.sub.11                                             6.8    CF.sub.3                                                                              sec.-C.sub.5 H.sub.11                                          6.9    CF.sub.3                                                                              n-C.sub.6 H.sub.13                                             6.10   CF.sub.3                                                                              n-C.sub.7 H.sub.15                                             6.11   CF.sub.3                                                                              sec.-C.sub.7 H.sub.15                                          6.12   CF.sub.3                                                                              1-Methylvinyl                                                  6.13   CF.sub.3                                                                              2-Methylvinyl                                                  6.14   CF.sub.3                                                                              Allyl                                                          6.15   CF.sub.3                                                                              2-Methylallyl                                                  6.16   CF.sub.3                                                                              2-Ethylallyl                                                   6.17   CF.sub.3                                                                              1-Methylallyl                                                  6.18   CF.sub.3                                                                              1-Ethylallyl                                                   6.19   CF.sub.3                                                                              1-Methyl-2-butenyl                                             6.20   CF.sub.3                                                                              1-Ethyl-2-butenyl                                              6.21   CF.sub.3                                                                              1-Isopropyl-2-butenyl                                          6.22   CF.sub.3                                                                              1-n-Butyl-2-butenyl                                            6.23   CF.sub.3                                                                              1-Methyl-2-pentenyl                                            6.24   CF.sub.3                                                                              1,4-Dimethyl-2-pentenyl                                        6.25   CF.sub.3                                                                              Propargyl                                                      6.26   CF.sub.3                                                                              2-butynyl                                                      6.27   CF.sub.3                                                                              3-butynyl                                                      6.28   CF.sub.3                                                                              Ethoxy                                                         6.29   CF.sub.3                                                                              Propoxy                                                        6.30   CF.sub.3                                                                              1-Methylethoxy                                                 6.31   CF.sub.3                                                                              n-Butoxy                                                       6.32   CF.sub.3                                                                              1-Methylpropoxy                                                6.33   CF.sub.3                                                                              2-Methylpropoxy                                                6.34   CF.sub.3                                                                              1,1-Dimethylethoxy                                             6.35   CF.sub.3                                                                              n-Pentyloxy                                                    6.36   CF.sub.3                                                                              n-Hexyloxy                                                     6.37   CF.sub.3                                                                              2-Ethylhexyloxy                                                6.38   CF.sub.3                                                                              2-Propenyloxy                                                  6.39   CF.sub.3                                                                              2-Butentyloxy                                                  6.40   CF.sub.3                                                                              2-Methyl-2-propenyloxy                                         6.41   CF.sub.3                                                                              2-Pentenyloxy                                                  6.42   CF.sub.3                                                                              3-Pentenyloxy                                                  6.43   CF.sub.3                                                                              3-chloro-2-propenyloxy                                         6.44   CF.sub.3                                                                              2,3-Dichloro-2-propenyloxy                                     6.45   CF.sub.3                                                                              2,3,3-Trichloro-propenyloxy                                    6.46   CF.sub.3                                                                              2-propynyloxy                                                  6.47   CF.sub.3                                                                              2-butynyl-oxy                                                  6.48   CF.sub.3                                                                              3-butynyl-oxy                                                  6.49   CF.sub.3                                                                              1-Methyl-2-propynyloxy                                         6.50   CF.sub.3                                                                              Cyclopropyl                                                    6.51   CF.sub.3                                                                              Cyclobutyl                                                     6.52   CF.sub.3                                                                              Cyclopentyl        150-152                                     6.53   CF.sub.3                                                                              Cyclohexyl         130-132                                     6.54   CF.sub.3                                                                              2-Cyclopentenyl    160-161                                     6.55   CF.sub.3                                                                              1-Cyclopentenyl                                                6.56   CF.sub.3                                                                              2-Cyclohexenyl     103-105                                     6.57   CF.sub.3                                                                              1-Cyclohexenyl                                                 6.58   CF.sub.3                                                                              Cyclopentyloxy                                                 6.59   CF.sub.3                                                                              Cyclohexyloxy                                                  6.60   CF.sub.3                                                                              2-Cyclopentenyloxy                                             6.61   CF.sub.3                                                                              2-Cyclohexenyloxy                                              ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                        Compounds of the formula V where A is A.sub.1                                  ##STR20##                                                                                                     Phys. data                                   No.    R.sup.1                                                                              R.sup.7            mp [°C.]                              ______________________________________                                        7.1    Cl     i-C.sub.3 H.sub.7  125-127                                      7.2    Cl     n-C.sub.3 H.sub.7  108-110                                      7.3    Cl     n-C.sub.4 H.sub.9                                               7.4    Cl     sec.-C.sub.4 H.sub.9                                                                             73-74                                        7.5    Cl     i-C.sub.4 H.sub.9  90-92                                        7.6    Cl     tert.-C.sub.4 H.sub.9                                           7.7    Cl     n-C.sub.5 H.sub.11                                              7.8    Cl     sec.-C.sub.5 H.sub.11                                           7.9    Cl     n-C.sub.6 H.sub.13                                              7.10   Cl     n-C.sub.7 H.sub.15                                              7.11   Cl     sec.-C.sub.7 H.sub.15                                           7.12   Cl     1-Methylvinyl                                                   7.13   Cl     2-Methylvinyl                                                   7.14   Cl     Allyl                                                           7.15   Cl     2-Methylallyl                                                   7.16   Cl     2-Ethylallyl                                                    7.17   Cl     1-Methylallyl                                                   7.18   Cl     1-Ethylallyl                                                    7.19   Cl     1-Methyl-2-butenyl                                              7.20   Cl     1-Ethyl-2-butenyl                                               7.21   Cl     1-Isopropyl-2-butenyl                                           7.22   Cl     1-n-Butyl-2-butenyl                                             7.23   Cl     1-Methyl-2-pentenyl                                             7.24   Cl     1,4-Dimethyl-2-pentenyl                                         7.25   Cl     Propargyl                                                       7.26   Cl     2-butynyl                                                       7.27   Cl     3-butynyl                                                       7.28   Cl     Ethoxy                                                          7.29   Cl     Propoxy                                                         7.30   Cl     1-Methylethoxy                                                  7.31   Cl     n-Butoxy                                                        7.32   Cl     1-Methylpropoxy                                                 7.33   Cl     2-Methylpropoxy                                                 7.34   Cl     1,1-Dimethylethoxy                                              7.35   Cl     n-Pentyloxy                                                     7.36   Cl     n-Hexyloxy                                                      7.37   Cl     2-Ethylhexyloxy                                                 7.38   Cl     2-Propenyloxy                                                   7.39   Cl     2-Butentyloxy                                                   7.40   Cl     2-Methyl-2-propenyloxy                                          7.41   Cl     2-Pentenyloxy                                                   7.42   Cl     3-Pentenyloxy                                                   7.43   Cl     3-chloro-2-propenyloxy                                          7.44   Cl     2,3-Dichloro-2-propenyloxy                                      7.45   Cl     2,3,3-Trichloro-propenyloxy                                     7.46   Cl     2-propynyloxy                                                   7.47   Cl     2-butynyl-oxy                                                   7.48   Cl     3-butynyl-oxy                                                   7.49   Cl     1-Methyl-2-propynyloxy                                          7.50   Cl     Cyclopropyl                                                     7.51   Cl     Cyclobutyl                                                      7.52   Cl     Cyclopentyl        110-111                                      7.53   Cl     Cyclohexyl         141-142                                      7.54   Cl     2-Cyclopentenyl    110-112                                      7.55   Cl     1-Cyclopentenyl                                                 7.56   Cl     2-Cyclohexenyl     84-86                                        7.57   Cl     1-Cyclohexenyl                                                  7.58   Cl     Cyclopentyloxy                                                  7.59   Cl     Cyclohexyloxy                                                   7.60   Cl     2-Cyclopentenyloxy                                              7.61   Cl     2-Cyclohexenyloxy                                               ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                        Compounds of the formula V where A is A.sub.2                                  ##STR21##                                                                                                     Phys. data                                   No.    n      R.sup.7            mp [°C.]                              ______________________________________                                        8.1    2      i-C.sub.3 H.sub.7                                               8.2    2      n-C.sub.3 H.sub.7                                               8.3    2      n-C.sub.4 H.sub.9                                               8.4    2      sec.-C.sub.4 H.sub.9                                                                             96-98                                        8.5    2      i-C.sub.4 H.sub.9  85-86                                        8.6    2      tert.-C.sub.4 H.sub.9                                           8.7    2      n-C.sub.5 H.sub.11                                              8.8    2      sec.-C.sub.5 H.sub.11                                           8.9    2      n-C.sub.6 H.sub.13                                              8.10   2      n-C.sub.7 H.sub.15                                              8.11   2      sec.-C.sub.7 H.sub.15                                           8.12   2      1-Methylvinyl                                                   8.13   2      2-Methylvinyl                                                   8.14   2      Allyl                                                           8.15   2      2-Methylallyl                                                   8.16   2      2-Ethylallyl                                                    8.17   2      1-Methylallyl                                                   8.18   2      1-Ethylallyl                                                    8.19   2      1-Methyl-2-butenyl                                              8.20   2      1-Ethyl-2-butenyl                                               8.21   2      1-Isopropyl-2-butenyl                                           8.22   2      1-n-Butyl-2-butenyl                                             8.23   2      1-Methyl-2-pentenyl                                             8.24   2      1,4-Dimethyl-2-pentenyl                                         8.25   2      Propargyl                                                       8.26   2      2-butynyl                                                       8.27   2      3-butynyl                                                       8.28   2      Ethoxy                                                          8.29   2      Propoxy                                                         8.30   2      1-Methylethoxy                                                  8.31   2      n-Butoxy                                                        8.32   2      1-Methylpropoxy    100-102                                      8.33   2      2-Methylpropoxy                                                 8.34   2      1,1-Dimethylethoxy                                              8.35   2      n-Pentyloxy                                                     8.36   2      n-Hexyloxy                                                      8.37   2      2-Ethylhexyloxy                                                 8.38   2      2-Propenyloxy                                                   8.39   2      2-Butentyloxy                                                   8.40   2      2-Methyl-2-propenyloxy                                          8.41   2      2-Pentenyloxy                                                   8.42   2      3-Pentenyloxy                                                   8.43   2      3-chloro-2-propenyloxy                                          8.44   2      2,3-Dichloro-2-propenyloxy                                      8.45   2      2,3,3-Trichloro-propenyloxy                                     8.46   2      2-propynyloxy                                                   8.47   2      2-butynyl-oxy                                                   8.48   2      3-butynyl-oxy                                                   8.49   2      1-Methyl-2-propynyloxy                                          8.50   2      Cyclopropyl                                                     8.51   2      Cyclobutyl                                                      8.52   2      Cyclopentyl        128-130                                      8.53   2      Cyclohexyl         134-135                                      8.54   2      2-Cyclopentenyl                                                 8.55   2      1-Cyclopentenyl                                                 8.56   2      2-Cyclohexenyl                                                  8.57   2      1-Cyclohexenyl                                                  8.58   2      Cyclopentyloxy                                                  8.59   2      Cyclohexyloxy                                                   8.60   2      2-Cyclopentenyloxy                                              8.61   2      2-Cyclohexenyloxy                                               8.62   1      i-C.sub.3 H.sub.7                                               8.63   1      n-C.sub.3 H.sub.7                                               8.64   1      n-C.sub.4 H.sub.9                                               8.65   1      sec.-C.sub.4 H.sub.9                                                                             oil                                          8.66   1      i-C.sub.4 H.sub.9  oil                                          8.67   1      tert.-C.sub.4 H.sub.9                                           8.68   1      n-C.sub.5 H.sub.11                                              8.69   1      sec.-C.sub.5 H.sub.11                                           8.70   1      n-C.sub.6 H.sub.13                                              8.71   1      n-C.sub.7 H.sub.15                                              8.72   1      sec.-C.sub.7 H.sub.15                                           8.73   1      Ethoxy                                                          8.74   1      Propoxy                                                         8.75   1      1-Methylethoxy                                                  8.76   1      n-Butoxy                                                        8.77   1      1-Methylpropoxy                                                 8.78   1      2-Methylpropoxy                                                 8.79   1      1,1-Dimethylethoxy                                              8.80   1      n-Pentyloxy                                                     8.81   1      n-Hexyloxy                                                      8.82   1      Cyclopentyl                                                     ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                        Compounds of the formula V where A is A.sub.4                                  ##STR22##                                                                                                        Phys. data                                No.  R.sup.3                                                                              R.sup.4                                                                              R.sup.7          mp [°C.]                           ______________________________________                                        9.1  CF.sub.3                                                                             CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                              115-116                                   9.2  CF.sub.3                                                                             CH.sub.3                                                                             n-C.sub.3 H.sub.7                                                                              114-116                                   9.3  CF.sub.3                                                                             CH.sub.3                                                                             n-C.sub.4 H.sub.9                                          9.4  CF.sub.3                                                                             CH.sub.3                                                                             sec.-C.sub.4 H.sub.9                                                                           73-75                                     9.5  CF.sub.3                                                                             CH.sub.3                                                                             i-C.sub.4 H.sub.9                                                                              100-102                                   9.6  CF.sub.3                                                                             CH.sub.3                                                                             tert.-C.sub.4 H.sub.9                                      9.7  CF.sub.3                                                                             CH.sub.3                                                                             n-C.sub.5 H.sub.11                                         9.8  CF.sub.3                                                                             CH.sub.3                                                                             sec.-C.sub.5 H.sub.11                                      9.9  CF.sub.3                                                                             CH.sub.3                                                                             n-C.sub.6 H.sub.13                                         9.10 CF.sub.3                                                                             CH.sub.3                                                                             n-C.sub.7 H.sub.15                                         9.11 CF.sub.3                                                                             CH.sub.3                                                                             sec.-C.sub.7 H.sub.15                                      9.12 CF.sub.3                                                                             CH.sub.3                                                                             1-Methylvinyl                                              9.13 CF.sub.3                                                                             CH.sub.3                                                                             2-Methylvinyl                                              9.14 CF.sub.3                                                                             CH.sub.3                                                                             Allyl                                                      9.15 CF.sub.3                                                                             CH.sub.3                                                                             2-Methylallyl                                              9.16 CF.sub.3                                                                             CH.sub.3                                                                             2-Ethylallyl                                               9.17 CF.sub.3                                                                             CH.sub. 3                                                                            1-Methylallyl                                              9.18 CF.sub.3                                                                             CH.sub.3                                                                             1-Ethylallyl                                               9.19 CF.sub.3                                                                             CH.sub.3                                                                             1-Methyl-2-butenyl                                         9.20 CF.sub.3                                                                             CH.sub.3                                                                             1-Ethyl-2-butenyl                                          9.21 CF.sub.3                                                                             CH.sub.3                                                                             1-Isopropyl-2-butenyl                                      9.22 CF.sub.3                                                                             CH.sub.3                                                                             1-n-Butyl-2-butenyl                                        9.23 CF.sub.3                                                                             CH.sub.3                                                                             1-Methyl-2-pentenyl                                        9.24 CF.sub.3                                                                             CH.sub.3                                                                             1,4-Dimethyl-2-pentenyl                                    9.25 CF.sub.3                                                                             CH.sub.3                                                                             Propargyl                                                  9.26 CF.sub.3                                                                             CH.sub.3                                                                             2-butynyl                                                  9.27 CF.sub.3                                                                             CH.sub.3                                                                             3-butynyl                                                  9.28 CF.sub.3                                                                             CH.sub.3                                                                             Ethoxy                                                     9.29 CF.sub.3                                                                             CH.sub.3                                                                             Propoxy                                                    9.30 CF.sub.3                                                                             CH.sub.3                                                                             1-Methylethoxy                                             9.31 CF.sub.3                                                                             CH.sub.3                                                                             n-Butoxy                                                   9.32 CF.sub.3                                                                             CH.sub.3                                                                             1-Methylpropoxy                                            9.33 CF.sub.3                                                                             CH.sub.3                                                                             2-Methylpropoxy                                            9.34 CF.sub.3                                                                             CH.sub.3                                                                             1,1-Dimethylethoxy                                         9.35 CF.sub.3                                                                             CH.sub.3                                                                             n-Pentyloxy                                                9.36 CF.sub.3                                                                             CH.sub.3                                                                             n-Hexyloxy                                                 9.37 CF.sub.3                                                                             CH.sub.3                                                                             2-Ethylhexyloxy                                            9.38 CF.sub.3                                                                             CH.sub.3                                                                             2-Propenyloxy                                              9.39 CF.sub.3                                                                             CH.sub.3                                                                             2-Butentyloxy                                              9.40 CF.sub.3                                                                             CH.sub.3                                                                             2-Methyl-2-propenyloxy                                     9.41 CF.sub.3                                                                             CH.sub.3                                                                             2-Pentenyloxy                                              9.42 CF.sub.3                                                                             CH.sub.3                                                                             3-Pentenyloxy                                              9.43 CF.sub.3                                                                             CH.sub.3                                                                             3-chloro-2-propenyloxy                                     9.44 CF.sub.3                                                                             CH.sub.3                                                                             2,3-Dichloro-2-propenyloxy                                 9.45 CF.sub.3                                                                             CH.sub.3                                                                             2,3,3-Trichloro-propenyloxy                                9.46 CF.sub.3                                                                             CH.sub.3                                                                             2-propynyloxy                                              9.47 CF.sub.3                                                                             CH.sub.3                                                                             2-butynyl-oxy                                              9.48 CF.sub.3                                                                             CH.sub.3                                                                             3-butynyl-oxy                                              9.49 CF.sub.3                                                                             CH.sub.3                                                                             1-Methyl-2-propynyloxy                                     9.50 CF.sub.3                                                                             CH.sub.3                                                                             Cyclopropyl                                                9.51 CF.sub.3                                                                             CH.sub.3                                                                             Cyclobutyl                                                 9.52 CF.sub.3                                                                             CH.sub.3                                                                             Cyclopentyl      114-118                                   9.53 CF.sub.3                                                                             CH.sub.3                                                                             Cyclohexyl       100-104                                   9.54 CF.sub.3                                                                             CH.sub.3                                                                             2-Cyclopentenyl  116-120                                   9.55 CF.sub.3                                                                             CH.sub.3                                                                             1-Cyclopentenyl                                            9.56 CF.sub.3                                                                             CH.sub.3                                                                             2-Cyclohexenyl   96-98                                     9.57 CF.sub.3                                                                             CH.sub.3                                                                             1-Cyclohexenyl                                             9.58 CF.sub.3                                                                             CH.sub.3                                                                             Cyclopentyloxy                                             9.59 CF.sub.3                                                                             CH.sub.3                                                                             Cyclohexyloxy                                              9.60 CF.sub.3                                                                             CH.sub.3                                                                             2-Cyclopentenyloxy                                         9.61 CF.sub.3                                                                             CH.sub.3                                                                             2-Cyclohexenyloxy                                          9.62 CH.sub.3                                                                             CH.sub.3                                                                             i-C.sub.3 H.sub.7                                          9.63 CH.sub.3                                                                             CH.sub.3                                                                             n-C.sub.3 H.sub.7                                          9.64 CH.sub.3                                                                             CH.sub.3                                                                             n-C.sub.4 H.sub.9                                          9.65 CH.sub.3                                                                             CH.sub.3                                                                             sec.-C.sub.4 H.sub.9                                                                           136                                       9.66 CH.sub.3                                                                             CH.sub.3                                                                             i-C.sub.4 H.sub.9                                                                              96-97                                     9.67 CH.sub.3                                                                             CH.sub.3                                                                             tert.-C.sub.4 H.sub.9                                      9.68 CH.sub.3                                                                             CH.sub.3                                                                             n-C.sub.5 H.sub.11                                         9.69 CH.sub.3                                                                             CH.sub.3                                                                             sec.-C.sub.5 H.sub.11                                      9.70 CH.sub.3                                                                             CH.sub.3                                                                             n-C.sub.6 H.sub.13                                         9.71 CH.sub.3                                                                             CH.sub.3                                                                             n-C.sub.7 H.sub.15                                         9.72 CH.sub.3                                                                             CH.sub.3                                                                             sec.-C.sub.7 H.sub.15                                      9.73 CH.sub.3                                                                             CH.sub.3                                                                             Ethoxy                                                     9.74 CH.sub.3                                                                             CH.sub.3                                                                             Propoxy                                                    9.75 CH.sub.3                                                                             CH.sub.3                                                                             1-Methylethoxy                                             9.76 CH.sub.3                                                                             CH.sub.3                                                                             n-Butoxy                                                   9.77 CH.sub.3                                                                             CH.sub.3                                                                             1-Methylpropoxy                                            9.78 CH.sub.3                                                                             CH.sub.3                                                                             2-Methylpropoxy                                            9.79 CH.sub.3                                                                             CH.sub.3                                                                             1,1-Dimethylethoxy                                         9.80 CH.sub.3                                                                             CH.sub.3                                                                             n-Pentyloxy                                                9.81 CH.sub.3                                                                             CH.sub.3                                                                             n-Hexyloxy                                                 9.82 CH.sub.3                                                                             CH.sub.3                                                                             Cyclopentyl      128-130                                   9.83 CH.sub.3                                                                             CH.sub.3                                                                             Cyclopentenyl    128-129                                   9.84 CH.sub.3                                                                             CH.sub.3                                                                             Cyclohexyl       128-129                                   9.85 CH.sub.3                                                                             CH.sub.3                                                                             1-Ethyl-propoxy  45-47                                     9.86 CH.sub.3                                                                             CH.sub.3                                                                             Cyclopentyloxy   97-99                                     9.87 CH.sub.3                                                                             CH.sub.3                                                                             2-Cyclohexenyloxy                                                                              87-89                                     9.88 CH.sub.3                                                                             CH.sub.3                                                                             2-Methyl-2-propenyloxy                                                                         103-105                                   ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                        Compounds of the formula V where A is A.sub.6                                  ##STR23##                                                                                                        Phys. data                                No.  R.sup.5                                                                              R.sup.6                                                                              R.sup.7          mp [°C.]                           ______________________________________                                        10.1 CH.sub.3                                                                             Cl     i-C.sub.3 H.sub.7                                                                              108-110                                   10.2 CH.sub.3                                                                             Cl     n-C.sub.3 H.sub.7                                                                              129-130                                   10.3 CH.sub.3                                                                             Cl     n-C.sub.4 H.sub.9                                          10.4 CH.sub.3                                                                             Cl     sec.-C.sub.4 H.sub.9                                                                           71-73                                     10.5 CH.sub.3                                                                             Cl     i-C.sub.4 H.sub.9                                                                              119-120                                   10.6 CH.sub.3                                                                             Cl     tert.-C.sub.4 H.sub.9                                      10.7 CH.sub.3                                                                             Cl     n-C.sub.5 H.sub.11                                         10.8 CH.sub.3                                                                             Cl     sec.-C.sub.5 H.sub.11                                      10.9 CH.sub.3                                                                             Cl     n-C.sub.6 H.sub.13                                         10.10                                                                              CH.sub.3                                                                             Cl     n-C.sub.7 H.sub.15                                         10.11                                                                              CH.sub.3                                                                             Cl     sec.-C.sub.7 H.sub.15                                      10.12                                                                              CH.sub.3                                                                             Cl     1-Methylvinyl                                              10.13                                                                              CH.sub.3                                                                             Cl     2-Methylvinyl                                              10.14                                                                              CH.sub.3                                                                             Cl     Allyl                                                      10.15                                                                              CH.sub.3                                                                             Cl     2-Methylallyl                                              10.16                                                                              CH.sub.3                                                                             Cl     2-Ethylallyl                                               10.17                                                                              CH.sub.3                                                                             Cl     1-Methylallyl                                              10.18                                                                              CH.sub.3                                                                             Cl     1-Ethylallyl                                               10.19                                                                              CH.sub.3                                                                             Cl     1-Methyl-2-butenyl                                         10.20                                                                              CH.sub.3                                                                             Cl     1-Ethyl-2-butenyl                                          10.21                                                                              CH.sub.3                                                                             Cl     1-Isopropyl-2-butenyl                                      10.22                                                                              CH.sub.3                                                                             Cl     1-n-Butyl-2-butenyl                                        10.23                                                                              CH.sub.3                                                                             Cl     1-Methyl-2-pentenyl                                        10.24                                                                              CH.sub.3                                                                             Cl     1,4-Dimethyl-2-pentenyl                                    10.25                                                                              CH.sub.3                                                                             Cl     Propargyl                                                  10.26                                                                              CH.sub.3                                                                             Cl     2-butynyl                                                  10.27                                                                              CH.sub.3                                                                             Cl     3-butynyl                                                  10.28                                                                              CH.sub.3                                                                             Cl     Ethoxy                                                     10.29                                                                              CH.sub.3                                                                             Cl     Propoxy                                                    10.30                                                                              CH.sub.3                                                                             Cl     1-Methylethoxy                                             10.31                                                                              CH.sub.3                                                                             Cl     n-Butoxy                                                   10.32                                                                              CH.sub.3                                                                             Cl     1-Methylpropoxy                                            10.33                                                                              CH.sub.3                                                                             Cl     2-Methylpropoxy                                            10.34                                                                              CH.sub.3                                                                             Cl     1,1-Dimethylethoxy                                         10.35                                                                              CH.sub.3                                                                             Cl     n-Pentyloxy                                                10.36                                                                              CH.sub.3                                                                             Cl     n-Hexyloxy                                                 10.37                                                                              CH.sub.3                                                                             Cl     2-Ethylhexyloxy                                            10.38                                                                              CH.sub.3                                                                             Cl     2-Propenyloxy                                              10.39                                                                              CH.sub.3                                                                             Cl     2-Butentyloxy                                              10.40                                                                              CH.sub.3                                                                             Cl     2-Methyl-2-propenyloxy                                     10.41                                                                              CH.sub.3                                                                             Cl     2-Pentenyloxy                                              10.42                                                                              CH.sub.3                                                                             Cl     3-Pentenyloxy                                              10.43                                                                              CH.sub.3                                                                             Cl     3-chloro-2-propenyloxy                                     10.44                                                                              CH.sub.3                                                                             Cl     2,3-Dichloro-2-propenyloxy                                 10.45                                                                              CH.sub.3                                                                             Cl     2,3,3-Trichloro-propenyloxy                                10.46                                                                              CH.sub.3                                                                             Cl     2-propynyloxy                                              10.47                                                                              CH.sub.3                                                                             Cl     2-butynyl-oxy                                              10.48                                                                              CH.sub.3                                                                             Cl     3-butynyl-oxy                                              10.49                                                                              CH.sub.3                                                                             Cl     1-Methyl-2-propynyloxy                                     10.50                                                                              CH.sub.3                                                                             Cl     Cyclopropyl                                                10.51                                                                              CH.sub.3                                                                             Cl     Cyclobutyl                                                 10.52                                                                              CH.sub.3                                                                             Cl     Cyclopentyl      122-123                                   10.53                                                                              CH.sub.3                                                                             Cl     Cyclohexyl       143-144                                   10.54                                                                              CH.sub.3                                                                             Cl     2-Cyclopentenyl  123-125                                   10.55                                                                              CH.sub.3                                                                             Cl     1-Cyclopentenyl                                            10.56                                                                              CH.sub.3                                                                             Cl     2-Cyclohexenyl   114-116                                   10.57                                                                              CH.sub.3                                                                             Cl     1-Cyclohexenyl                                             10.58                                                                              CH.sub.3                                                                             Cl     Cyclopentyloxy                                             10.59                                                                              CH.sub. 3                                                                            Cl     Cyclohexyloxy                                              10.60                                                                              CH.sub.3                                                                             Cl     2-Cyclopentenyloxy                                         10.61                                                                              CH.sub.3                                                                             Cl     2-Cyclohexenyloxy                                          10.62                                                                              CF.sub.3                                                                             Cl     i-C.sub.3 H.sub.7                                          10.63                                                                              CF.sub.3                                                                             Cl     n-C.sub.3 H.sub.7                                          10.64                                                                              CF.sub.3                                                                             Cl     n-C.sub.4 H.sub.9                                          10.65                                                                              CF.sub.3                                                                             Cl     sec.-C.sub.4 H.sub.9                                                                           108-110                                   10.66                                                                              CF.sub.3                                                                             Cl     i-C.sub.4 H.sub.9                                                                              122-124                                   10.67                                                                              CF.sub.3                                                                             Cl     tert.-C.sub.4 H.sub.9                                      10.68                                                                              CF.sub.3                                                                             Cl     n-C.sub.5 H.sub.11                                         10.69                                                                              CF.sub.3                                                                             Cl     sec.-C.sub.5 H.sub.11                                      10.70                                                                              CF.sub.3                                                                             Cl     n-C.sub.6 H.sub.13                                         10.71                                                                              CF.sub.3                                                                             Cl     n-C.sub.7 H.sub.15                                         10.72                                                                              CF.sub.3                                                                             Cl     sec.-C.sub.7 H.sub.15                                      10.73                                                                              CF.sub.3                                                                             Cl     Ethoxy                                                     10.74                                                                              CF.sub.3                                                                             Cl     Propoxy                                                    10.75                                                                              CF.sub.3                                                                             Cl     1-Methylethoxy                                             10.76                                                                              CF.sub.3                                                                             Cl     n-Butoxy                                                   10.77                                                                              CF.sub.3                                                                             Cl     1-Methylpropoxy                                            10.78                                                                              CF.sub.3                                                                             Cl     2-Methylpropoxy                                            10.79                                                                              CF.sub.3                                                                             Cl     1,1-Dimethylethoxy                                         10.80                                                                              CF.sub.3                                                                             Cl     n-Pentyloxy                                                10.81                                                                              CF.sub.3                                                                             Cl     n-Hexyloxy                                                 10.82                                                                              CF.sub.3                                                                             Cl     Cyclopentyl      113-115                                   10.83                                                                              CF.sub.3                                                                             Cl     Cyclopentenyl    132-133                                   ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                        Compounds of the formula V where A is A.sub.7                                  ##STR24##                                                                                                      Phys. data                                  No.   R.sup.2                                                                              R.sup.6 R.sup.7      mp [°C.]                             ______________________________________                                        11.1  H      CH.sub.3                                                                              i-C.sub.3 H.sub.7                                        11.2  H      CH.sub.3                                                                              n-C.sub.3 H.sub.7                                        11.3  H      CH.sub.3                                                                              n-C.sub.4 H.sub.9                                        11.4  H      CH.sub.3                                                                              sec.-C.sub.4 H.sub.9                                                                       oil                                         11.5  H      CH.sub.3                                                                              i-C.sub.4 H.sub.9                                                                          oil                                         11.6  H      CH.sub.3                                                                              tert.-C.sub.4 H.sub.9                                    11.7  H      CH.sub.3                                                                              n-C.sub.5 H.sub.11                                       11.8  H      CH.sub.3                                                                              sec.-C.sub.5 H.sub.11                                    11.9  H      CH.sub.3                                                                              n-C.sub.6 H.sub.13                                       11.10 H      CH.sub.3                                                                              n-C.sub.7 H.sub.15                                       11.11 H      CH.sub.3                                                                              sec.-C.sub.7 H.sub.15                                    11.12 H      CH.sub.3                                                                              Ethoxy                                                   11.13 H      CH.sub.3                                                                              Propoxy                                                  11.14 H      CH.sub.3                                                                              1-Methylethoxy                                           11.15 H      CH.sub.3                                                                              n-Butoxy                                                 11.16 H      CH.sub.3                                                                              1-Methylpropoxy                                          11.17 H      CH.sub.3                                                                              2-Methylpropoxy                                          11.18 H      CH.sub.3                                                                              1,1-Dimethylethoxy                                       11.19 H      CH.sub.3                                                                              n-Pentyloxy                                              11.20 H      CH.sub.3                                                                              n-Hexyloxy                                               11.21 H      CH.sub.3                                                                              Cyclopentyl                                              11.22 H      CH.sub.3                                                                              Cyclopentenyl                                            ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                        Compounds of the formula V where A is A.sub.3                                  ##STR25##                                                                                                    Phys. data                                    No.     R.sup.2 R.sup.7         mp [°C.]                               ______________________________________                                        12.1    H       i-C.sub.3 H.sub.7                                                                             147-148                                       12.2    H       n-C.sub.3 H.sub.7                                             12.3    H       n-C.sub.4 H.sub.9                                             12.4    H       sec.-C.sub.4 H.sub.9                                                                          109-110                                       12.5    H       i-C.sub.4 H.sub.9                                                                             114-115                                       12.6    H       tert.-C.sub.4 H.sub.9                                         12.7    H       n-C.sub.5 H.sub.11                                            12.8    H       sec.-C.sub.5 H.sub.11                                         12.9    H       n-C.sub.6 H.sub.13                                            12.10   H       n-C.sub.7 H.sub.15                                            12.11   H       sec.-C.sub.7 H.sub.15                                         12.12   H       Ethoxy                                                        12.13   H       Propoxy                                                       12.14   H       1-Methylethoxy                                                12.15   H       n-Butoxy                                                      12.16   H       1-Methylpropoxy                                               12.17   H       2-Methylpropoxy                                               12.18   H       1,1-Dimethylethoxy                                            12.19   H       n-Pentyloxy                                                   12.20   H       n-Hexyloxy                                                    12.21   H       Cyclopentyl     97-98                                         12.22   H       Cyclohexyl      125-127                                       12.23   H       2-Cyclopentenyl 98-99                                         12.24   H       1-Cyclopentenyl                                               12.25   H       2-Cyclohexenyl  82-84                                         12.26   H       1-Cyclohexenyl                                                12.27   H       Cyclopentyloxy  73-75                                         12.28   H       Cyclohexyloxy                                                 12.29   H       2-Cyclopentenyloxy                                            12.30   CH.sub.3                                                                              i-C.sub.3 H.sub.7                                             12.31   CH.sub.3                                                                              n-C.sub.3 H.sub.7                                             12.32   CH.sub.3                                                                              n-C.sub.4 H.sub.9                                             12.33   CH.sub.3                                                                              sec.-C.sub.4 H.sub.9                                                                          80-82                                         12.34   CH.sub.3                                                                              i-C.sub.4 H.sub.9                                                                             114-116                                       12.35   CH.sub.3                                                                              tert.-C.sub.4 H.sub.9                                         12.36   CH.sub.3                                                                              n-C.sub.5 H.sub.11                                            12.37   CH.sub.3                                                                              sec.-C.sub.5 H.sub.11                                         12.38   CH.sub.3                                                                              n-C.sub.6 H.sub.13                                            12.39   CH.sub.3                                                                              n-C.sub.7 H.sub.15                                            12.40   CH.sub.3                                                                              sec.-C.sub.7 H.sub.15                                         12.41   CH.sub.3                                                                              Ethoxy                                                        12.42   CH.sub.3                                                                              Propoxy                                                       12.43   CH.sub.3                                                                              1-Methylethoxy                                                12.44   CH.sub.3                                                                              n-Butoxy                                                      12.45   CH.sub.3                                                                              1-Methylpropoxy                                               12.46   CH.sub.3                                                                              2-Methylpropoxy                                               12.47   CH.sub.3                                                                              1,1-Dimethylethoxy                                            12.48   CH.sub.3                                                                              n-Pentyloxy                                                   12.49   CH.sub.3                                                                              n-Hexyloxy                                                    12.50   CH.sub.3                                                                              Cyclopentyl                                                   12.51   H       2-Methyl-2-propenyloxy                                                                        40-41                                         12.52   H       1-Ethyl-propoxy oil                                           12.53   H       2-Cyclohexenyloxy                                                                             51-53                                         ______________________________________                                    

Manufacturing examples EXAMPLE 7

At 0° C., 2.3 g of 2-methyl-4-trifluoromethyl-thiazole-5-carboxylicchloride is dripped into a solution of 1.4 g of 2-n-propylaniline and1.1 g of triethylamine in 15 ml of tetrahydrofuran, and the mixture isstirredfor 12 hours at 20° C.

After dilution with 300 ml of water, extraction with methyltert.-butylether (2×70 ml), evaporation of the solvent and mixture of the residuewith a small amount of n-pentane, there is isolated 2.8 g of2-methyl-4-trifluoromethyl-thiazole-5-carboxylicacid-2-n-propyl-anilide; m.p.: 114°-116° C. (Table 9, No. 2).

EXAMPLE 8

At 0° C., 3.8 g of 1,3-dimethyl-5-chloroopyrazole-4-carboxylic chlorideis dripped into a solution of 2.7 g of 2-isopropylamine and 2.2 goftriethylamine in 40 ml of dichloromethane, and the mixture is stirredfor 2 hours at 0° C. After washing with 50 ml of water, evaporationofthe solvent and recrystallization from cyclohexane there is isolated3.3g of 1,3-dimethyl-5-chloropyrazole-4-carboxylicacid-2-isopropylanilide,; m.p. 108°-110° C. (Table 10, No. 1).

                  TABLE 13                                                        ______________________________________                                        Compounds of the formula V where A is A.sub.1                                  ##STR26##                                                                                                     Phys. data                                   No.     R.sup.1                                                                              R.sup.7           mp [°C.]                              ______________________________________                                        13.1    Br     i-C.sub.3 H.sub.7                                              13.2    Br     n-C.sub.3 H.sub.7                                              13.3    Br     n-C.sub.4 H.sub.9                                              13.4    Br     sec.-C.sub.4 H.sub.9                                                                            74-75                                        13.5    Br     i-C.sub.4 H.sub.9 110-112                                      13.6    Br     tert.-C.sub.4 H.sub.9                                          13.7    Br     n-C.sub.5 H.sub.11                                             13.8    Br     sec.-C.sub.5 H.sub.11                                          13.9    Br     n-C.sub.6 H.sub.13                                             13.10   Br     n-C.sub.7 H.sub.15                                             13.11   Br     sec.-C.sub.7 H.sub.15                                          13.12   Br     1-Methylvinyl                                                  13.13   Br     2-Methylvinyl                                                  13.14   Br     Allyl                                                          13.15   Br     2-Methylallyl                                                  13.16   Br     2-Ethylallyl                                                   13.17   Br     1-Methylallyl                                                  13.18   Br     1-Ethylallyl                                                   13.19   Br     1-Methyl-2-butenyl                                             13.20   Br     1-Ethyl-2-butenyl                                              13.21   Br     1-Isopropyl-2-butenyl                                          13.22   Br     1-n-Butyl-2-butenyl                                            13.23   Br     1-Methyl-2-pentenyl                                            13.24   Br     1,4-Dimethyl-2-pentenyl                                        13.25   Br     Propargyl                                                      13.26   Br     2-butynyl                                                      13.27   Br     3-butynyl                                                      13.28   Br     Ethoxy                                                         13.29   Br     Propoxy                                                        13.30   Br     1-Methylethoxy                                                 13.31   Br     n-Butoxy                                                       13.32   Br     1-Methylpropoxy                                                13.33   Br     2-Methylpropoxy                                                13.34   Br     1,1-Dimethylethoxy                                             13.35   Br     n-Pentyloxy                                                    13.36   Br     n-Hexyloxy                                                     13.37   Br     2-Ethylhexyloxy                                                13.38   Br     2-Propenyloxy                                                  13.39   Br     2-Butentyloxy                                                  13.40   Br     2-Methyl-2-propenyloxy                                         13.41   Br     2-Pentenyloxy                                                  13.42   Br     3-Pentenyloxy                                                  13.43   Br     3-chloro-2-propenyloxy                                         13.44   Br     2,3-Dichloro-2-propenyloxy                                     13.45   Br     2,3,3-Trichloro-propenyloxy                                    13.46   Br     2-propynyloxy                                                  13.47   Br     2-butynyl-oxy                                                  13.48   Br     3-butynyl-oxy                                                  13.49   Br     1-Methyl-2-propynyloxy                                         13.50   Br     Cyclopropyl                                                    13.51   Br     Cyclobutyl                                                     13.52   Br     Cyclopentyl                                                    13.53   Br     Cyclohexyl                                                     13.54   Br     2-Cyclopentenyl                                                13.55   Br     1-Cyclopentenyl                                                13.56   Br     2-Cyclohexenyl                                                 13.57   Br     1-Cyclohexenyl                                                 13.58   Br     Cyclopentyloxy                                                 13.59   Br     Cyclohexyloxy                                                  13.60   Br     2-Cyclopentenyloxy                                             13.61   Br     2-Cyclohexenyloxy                                              ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                        Compounds of the formula V where A is A.sub.1                                  ##STR27##                                                                                                     Phys. data                                   No.     R.sup.1                                                                              R.sup.7           mp [°C.]                              ______________________________________                                        14.1    I      i-C.sub.3 H.sub.7                                              14.2    I      n-C.sub.3 H.sub.7                                              14.3    I      n-C.sub.4 H.sub.9                                              14.4    I      sec.-C.sub.4 H.sub.9                                                                            97-98                                        14.5    I      i-C.sub.4 H.sub.9 148-149                                      14.6    I      tert.-C.sub.4 H.sub.9                                          14.7    I      n-C.sub.5 H.sub.11                                             14.8    I      sec.-C.sub.5 H.sub.11                                          14.9    I      n-C.sub.6 H.sub.13                                             14.10   I      n-C.sub.7 H.sub.15                                             14.11   I      sec.-C.sub.7 H.sub.15                                          14.12   I      1-Methylvinyl                                                  14.13   I      2-Methylvinyl                                                  14.14   I      Allyl                                                          14.15   I      2-Methylallyl                                                  14.16   I      2-Ethylallyl                                                   14.17   I      1-Methylallyl                                                  14.18   I      1-Ethylallyl                                                   14.19   I      1-Methyl-2-butenyl                                             14.20   I      1-Ethyl-2-butenyl                                              14.21   I      1-Isopropyl-2-butenyl                                          14.22   I      1-n-Butyl-2-butenyl                                            14.23   I      1-Methyl-2-pentenyl                                            14.24   I      1,4-Dimethyl-2-pentenyl                                        14.25   I      Propargyl                                                      14.26   I      2-butynyl                                                      14.27   I      3-butynyl                                                      14.28   I      Ethoxy                                                         14.29   I      Propoxy                                                        14.30   I      1-Methylethoxy                                                 14.31   I      n-Butoxy                                                       14.32   I      1-Methylpropoxy                                                14.33   I      2-Methylpropoxy                                                14.34   I      1,1-Dimethylethoxy                                             14.35   I      n-Pentyloxy                                                    14.36   I      n-Hexyloxy                                                     14.37   I      2-Ethylhexyloxy                                                14.38   I      2-Propenyloxy                                                  14.39   I      2-Butentyloxy                                                  14.40   I      2-Methyl-2-propenyloxy                                         14.41   I      2-Pentenyloxy                                                  14.42   I      3-Pentenyloxy                                                  14.43   I      3-chloro-2-propenyloxy                                         14.44   I      2,3-Dichloro-2-propenyloxy                                     14.45   I      2,3,3-Trichloro-propenyloxy                                    14.46   I      2-propynyloxy                                                  14.47   I      2-butynyl-oxy                                                  14.48   I      3-butynyl-oxy                                                  14.49   I      1-Methyl-2-propynyloxy                                         14.50   I      Cyclopropyl                                                    14.51   I      Cyclobutyl                                                     14.52   I      Cyclopentyl                                                    14.53   I      Cyclohexyl                                                     14.54   I      2-Cyclopentenyl                                                14.55   I      1-Cyclopentenyl                                                14.56   I      2-Cyclohexenyl                                                 14.57   I      1-Cyclohexenyl                                                 14.58   I      Cyclopentyloxy                                                 14.59   I      Cyclohexyloxy                                                  14.60   I      2-Cyclopentenyloxy                                             14.61   I      2-Cyclohexenyloxy                                              ______________________________________                                    

                  TABLE 15                                                        ______________________________________                                        Compounds of the formula V where A is A.sub.3                                  ##STR28##                                                                                               Phys. data                                         No.      R.sup.7           mp [°C.]                                    ______________________________________                                        15.1     i-C.sub.3 H.sub.7                                                    15.2     n-C.sub.3 H.sub.7                                                    15.3     n-C.sub.4 H.sub.9                                                    15.4     sec.-C.sub.4 H.sub.9                                                                            78-80                                              15.5     i-C.sub.4 H.sub.9 106-107                                            15.6     tert.-C.sub.4 H.sub.9                                                15.7     n-C.sub.5 H.sub.11                                                   15.8     sec.-C.sub.5 H.sub.11                                                15.9     n-C.sub.6 H.sub.13                                                   15.10    n-C.sub.7 H.sub.15                                                   15.11    sec.-C.sub.7 H.sub.15                                                15.12    Ethoxy                                                               15.13    Propoxy                                                              15.14    1-Methylethoxy                                                       15.15    n-Butoxy                                                             15.16    1-Methylpropoxy                                                      15.17    2-Methylpropoxy                                                      15.18    1,1-Dimethylethoxy                                                   15.19    n-Pentyloxy                                                          15.20    n-Hexyloxy                                                           15.21    Cyclopentyl                                                          15.22    Cyclohexyl                                                           15.23    2-Cyclopentenyl                                                      15.24    1-Cyclopentenyl                                                      15.25    2-Cyclohexenyl                                                       15.26    1-Cyclohexenyl                                                       15.27    Cyclopentyloxy                                                       15.28    Ethoxy                                                               15.29    Propoxy                                                              15.30    1-Methylethoxy                                                       15.31    n-Butoxy                                                             15.32    1-Methylpropoxy                                                      15.33    2-Methylpropoxy                                                      15.34    1,1-Dimethylethoxy                                                   15.35    n-Pentyloxy                                                          15.36    n-Hexyloxy                                                           15.37    2-Ethylhexyloxy                                                      15.38    2-Propenyloxy                                                        15.39    2-Butentyloxy                                                        15.40    2-Methyl-2-propenyloxy                                                                          oil                                                15.41    2-Pentenyloxy                                                        15.42    3-Pentenyloxy                                                        15.43    3-chloro-2-propenyloxy                                               15.44    2,3-Dichloro-2-propenyloxy                                           15.45    2,3,3-Trichloropropenyloxy                                           15.46    2-Propynyloxy                                                        15.47    2-Butynyl-oxy                                                        15.48    3-Butynyl-oxy                                                        15.49    1-Methyl-2-propynyloxy                                               15.50    Cyclopropyl                                                          15.51    Cyclobutyl                                                           15.52    Cyclopentyl                                                          15.53    Cyclohexyl                                                           15.54    2-Cyclopentenyl                                                      15.55    1-Cyclopentenyl                                                      15.56    2-Cyclohexenyl                                                       15.57    1-Cyclohexenyl                                                       15.58    Cyclopentyloxy    oil                                                15.59    Cyclohexyloxy                                                        15.60    2-Cyclopentenyloxy                                                   15.61    2-Cyclohexenyloxy oil                                                15.62    1-Ethylpropoxy    oil                                                ______________________________________                                    

The invention further relates to the following novel compounds.

Nicotinic anilide derivatives of the general formula I ##STR29##wherethe substituents have the following meanings:

R¹ halogen, methyl, trifluoromethyl, methoxy, methylthio,methylsulfinyl, methylsuflonyl,

R² unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted orhalogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, C₃ -C₆-cycloalkyl, C₄ -C₆ -cycloalkenyl, C₅ -C₆ -cycloalkyloxy, C₅ -C₆-cycloalkenyloxy, with the proviso that R² is not isopropyl when R¹ ischlorine.

Anilide derivatives of the general formula II ##STR30##where thesubstituents have the following meanings: ##STR31##

X methylene or sulfur

R unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted orhalogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyloxy, C₅ -C₁₂ -alkynyloxy,unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl,unsubstituted orC₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl,unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy,unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy

with the proviso that

A is not A₁ when R is ethoxy, isopropoxy or allyloxy,

A is not A₂, X denoting sulfur, when R is ethoxy, propoxy, n-butoxy,sec.-butoxy or n-pentyloxy,

A is not A₂, X denoting methylene, when R is isopropyl.

2-Aminobiphenyl derivatives of the general formula III, ##STR32##wherethe substituents have the following meanings: ##STR33##

X methylene, sulfur, sulfinyl, sulfonyl (SO₂),

R¹ methyl, trifluoromethyl, chlorine, bromine, iodine,

R² trifluoromethyl, chlorine

R³ hydrogen or methyl

R⁴ methyl, trifluoromethyl, chlorine

R⁵ hydrogen, methyl, chlorine

R⁶ methyl, trifluoromethyl

R⁷ methyl, chlorine

R⁸ C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄-alkylthio, halogen.

Carboxanilide derivatives of the general formula V ##STR34##where thesubstituents have the following meanings: ##STR35##

n 1 or 2

R¹ trifluoromethyl, chlorine, bromine, iodine,

R² hydrogen or methyl

R³ methyl, trifluoromethyl, chlorine

R⁴ hydrogen, methyl, chlorine

R⁵ methyl, trifluoromethyl

R⁶ methyl, chlorine

R⁷ unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted orhalogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy,unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl,unsubstituted orC₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl,unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy,unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy, withthe proviso that R⁷ is not 3-methylbut-2-en-1-yl or3-methyl-but-3-en-1-yl when R¹ is trifluoromethyl.

The novel compounds are suitable as fungicides.

The fungicidal compounds according to the invention, or agentscontaining them, may be applied for instance in the form of directlysprayable solutions, powders, suspensions (including high-percentageaqueous, oily or other suspensions), dispersions, emulsions, oildispersions, pastes, dusts, broadcasting agents, or granules byspraying, atomizing, dusting, broadcasting or watering. The forms ofapplication depend entirely on the purpose for which the agents arebeing used, but they must ensure as fine a distribution of the activeingredients according to the invention as possible.

Normally, the plants are sprayed or dusted with the active ingredients,or the seeds of the plants are treated with the active ingredients.

The formulations are produced in known manner, for example by extendingtheactive ingredient with solvents and/or carriers, with or without theuse ofemulsifiers and dispersants; if water is used as solvent, it isalso possible to employ other organic solvents as auxiliary solvents.Suitable auxiliaries for this purpose are solvents such as aromatics(e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins(e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones(e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide),and water;carriers such as ground natural minerals (e.g., kaolins,aluminas, talc andchalk) and ground synthetic minerals (e.g., highlydisperse silica and silicates); emulsifiers such as nonionic and anionicemulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkylsulfonates and aryl sulfonates); and dispersants such as lignin-sulfitewaste liquors and methylcellulose.

Examples of surfactants are: alkali metal, alkaline earth metal andammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid,phenolsulfonic acid, naphthalenesulfonic acid anddibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, andsalts of sulfated hexadecanols, heptadecanols, and octadecanols, saltsof fatty alcohol glycol ethers, condensation products of sulfonatednaphthalene andnaphthalene derivatives with formaldehyde, condensationproducts of naphthalene or naphthalenesulfonic acids with phenol andformaldehyde, polyoxyethylene octylphenol ethers, ethoxylatedisooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol,alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers,alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcoholethylene oxide condensates, ethoxylated castor oil, polyoxyethylenealkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycolether acetal, sorbitol esters,lignin-sulfite waste liquors and methylcellulose.

Examples of surfactants are: alkali metal, alkaline earth metal andammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid,phenolsulfonic acid, naphthalenesulfonic acid anddibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, andsalts of sulfated hexadecanols, heptadecanols, and octadecanols, saltsof fatty alcohol glycol ethers, condensation products of sulfonatednaphthalene andnaphthalene derivatives with formaldehyde, condensationproducts of naphthalene or naphthalenesulfonic acids with phenol andformaldehyde, polyoxyethylene octylphenol ethers, ethoxylatedisooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol,alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers,alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcoholethylene oxide condensates, ethoxylated castor oil, polyoxyethylenealkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycolether acetal, sorbitol esters,lignin-sulfite waste liquors and methylcellulose.

Powders, dusts and broadcasting agents may be prepared by mixing orgrinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may beprepared by bonding the active ingredients to solid carriers. Examplesof solid carriers are mineral earths such as silicic acids, silica gels,silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole,loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesiumsulfate, magnesium oxide, ground plastics, fertilizers such as ammoniumsulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetableproducts such as grain meals, bark meal, wood meal, and nutshell meal,cellulosic powders, etc.

Examples of formulations are given below.

I. A solution of 90 parts by weight of compound no. 1.7 and 10 parts byweight of N-methyl-α-pyrrolidone, which is suitable for application inthe form of very fine drops.

II. A mixture of 20 parts by weight of compound no. 1.8, 80 parts byweightof xylene, 10 parts by weight of the adduct of 8 to 10 moles ofethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts byweight of the calcium salt of dodecylbenzenesulfonic acid, and 5 partsby weight of the adduct of 40 moles of ethylene oxide and 1 mole ofcastor oil. By finely dispersing the mixture in water, an aqueousdispersion is obtained.

III. An aqueous dispersion of 20 parts by weight of compound no. 1.3, 40parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20parts by weight of the adduct of 40 moles of ethylene oxide and 1 moleof castor oil.

IV. An aqueous dispersion of 20 parts by weight of compound no. 1.4, 25parts by weight of cyclohexanol, 65 parts by weight of a mineral oilfraction having a boiling point between 210 and 280° C., and 10 parts byweight of the adduct of 40 moles of ethylene oxide and 1 mole of castoroil.

V. A hammer-milled mixture of 80 parts by weight of compound no. 1.5, 3parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonicacid, 10 parts by weight of the sodium salt of a lignin-sulfonic acidobtained from a sulfite waste liquor, and 7 parts by weight of powderedsilica gel. By finely dispersingthe mixture in water, a spray liquor isobtained.

VI. An intimate mixture of 3 parts by weight of compound no. 1.7 and 97parts by weight of particulate kaolin. The dust contains 3wt % of theactive ingredient.

VII. An intimate mixture of 30 parts by weight of compound no. 1.8, 92parts by weight of powdered silica gel and 8 parts by weight of paraffinoil sprayed onto the surface of this silica gel. This formulation of theactive ingredient exhibits good adherence.

VIII. A stable aqueous dispersion of 40 parts by weight of compound no.1.9, 10 parts by weight of the sodium salt of a phenolsulfonicacid-urea-formaldehyde condensate, 2 parts by weight of silica gel and48 parts by weight of water, which dispersion can be further diluted.

IX. A stable oily dispersion of 20 parts by weight of compound no. 1.33,2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8parts by weight of a fatty alcohol polyglycol ether, 20 parts by weightofthe sodium salt of a phenolsulfonic acid-urea-formaldehyde condensateand 68 parts by weight of a paraffinic mineral oil.

The novel compounds are extremely effective on a broad spectrum ofphytopathogenic fungi, in particular Botrytis. Some of them have asystemic action and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling alargenumber of fungi in various crops or their seeds, especially wheat,rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee,sugar cane, fruit and ornamentals in horticulture and viticulture, andin vegetables such as cucumbers, beans and cucurbits.

The compounds are applied by treating the fungi or the seeds, plants ormaterials threatened by fungus attack, or the soil with a fungicidallyeffective amount of the active ingredients.

The agents may be applied before or after infection of the materials,plants or seeds by the fungi.

The novel compounds are particularly useful for controlling thefollowing plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Fusarium and Verticillium species in various plants,

Alternaria species in fruit and vegetables.

Use against Botrytis is preferred.

The novel compounds may also be used for protecting materials (timber),e.g., against Paecilomyces variotii.

The fungicidal agents generally contain from 0.1 to 95, and preferablyfrom0.5 to 90, wt % of active ingredient.

The application rates depend on the type of effect desired, and rangefrom 0.02 to 3 kg of active ingredient per hectare.

When the active ingredients are used for treating seed, rates of 0.001to 50, and preferably from 0.01 to 10, g per kg of seed are generallysufficient.

In these application forms, the agents according to the invention mayalso be present together with other active ingredients, for exampleherbicides,insecticides, growth regulators, and other fungicides, andmay furthermore be mixed and applied together with fertilizers.Admixture with other fungicides frequently results in a greaterfungicidal action spectrum.

The following list of fungicides with which the novel compounds may becombined is intended to illustrate possible combinations but not toimposeany restrictions.

Examples of fungicides which may be combined with the novel compoundsare:

sulfur,

dithiocarbamates and their derivatives, such as

ferric dimethyldithiocarbamate,

zinc dimethyldithiocarbamate,

zinc ethylenebisdithiocarbamate,

manganese ethylenebisdithiocarbamate,

manganese zinc ethylenediaminebisdithiocarbamate,

tetramethylthiuram disulfides,

ammonia complex of zinc N,N'-ethylenebisdithiocarbamate,

ammonia complex of zinc N,N'-propylenebisdithiocarbamate,

zinc N,N'-propylenebisdithiocarbamate and

N,N'-polypropylenebis(thiocarbamyl) disulfide;

nitro derivatives, such as

dinitro(1-methylheptyl)-phenyl crotonate,

2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate,

2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate and

diisopropyl 5-nitroisophthalate;

heterocyclic substances, such as

2-heptadecylimidazol-2-yl acetate,

2,4-dichloro-6-(o-chloroanilino)-s-triazine,

O,O-diethylphthalimidophosphonothioate,

5-amino-1-[-bis-(dimethylamino)-phosphinyl]-3-phenyl-1,2,4-triazole,

2,3-dicyano-1,4-dithioanthraquinone,

2-thio-1,3-dithio[4,5-b]quinoxaline,

methyl 1-(butylcarbamyl)-2-benzimidazolecarbamate,

2-methoxycarbonylaminobenzimidazole,

2-(fur-2-yl) -benzimidazole,

2-(thiazol-4-yl) benzimidazole,

N-(1,1,2,2-tetrachloroethylthio) -tetrahydrophthalimide,

N-trichloromethylthiotetrahydrophthalimide,

N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuric acid diamide,

5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,

2-thiocyanatomethylthiobenzothiazole,

1,4-dichloro-2,5-dimethoxybenzene,

4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone,

2-thiopyridine 1-oxide,

8-hydroxyquinoline and its copper salt,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne,

2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne 4,4'dioxide,

2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide,

2-methylfuran-3-carboxanilide,

2,5-dimethylfuran-3-carboxanilide,

2,4,5-trimethylfuran-3-carboxanilide,

2,5-dimethyl-N-cyclohexylfuran-3-carboxamide,

N-cyclohexyl-N-methoxy-2,5-diethylfuran-3-carboxamide,

2-methylbenzanilide,

2-iodobenzanilide,

N-formyl-N-morpholine-2,2,2-trichloroethylacetal,

piperazine-1,4-diylbis-(1-(2,2,2-trichloroethyl)-formamide),

1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,

2,6-dimethyl-N-tridecylmorpholine and its salts,

2,6-dimethyl-N-cyclododecylmorpholine and its salts,

N[3-(p-tert.-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine,

N-3-(p-tert.-butylphenyl)-2-methylpropyl,-piperidine,

1-2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl'-1H-1,2,4-triazole,

1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole,

N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea,

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-tri-azol-1-yl)-butan-2-one,

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan- 2-ol,

α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,

5-butyl-(2-dimethylamino-4-hydroxy-6-methyltpyrimidine,

bis-(p-chlorophenyl)-3-pyridinemethanol,

1,2-bis-(3-ethoxycarbonyl-2-thioureido)-benzene,

1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene,

and various fungicides, such as dodecylguanidine acetate,

3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutaramide,

hexachlorobenzene,

DL-methyl-N-(2,6-dimethylphenyl)-N-fur-2-yl alanate,

methyl DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanate,

N-(2,6-dimethylphenyl)-N-chloroacetyl-DL-2-aminobutyrolactoile,

methyl DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanate,

5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,

3-[3,5-dichlorophenyl]-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,

3-(3,5-dichlorophenyl)-1-isopropylcarbamylhydantoin,

N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,

2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamide,

1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole,

2,4-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol,

N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine,and

1-((bis-(4-fluorophenyl)-methylsilyl)-methyl)-1H-1,2,4-triazole.

Use examples

The active ingredients 2-chloronicotic acid-2'-ethylanilide(A)--disclosed in U.S. Pat. No. 4,001,416 -- and 2-chloronicoticacid-3'-isopropylanilide(B)--disclosed in DE 26 11 601 --were used forcomparison purposes.

Use Example 1 Action on Botrytis cinerea in paprika

Slices of green paprika pods were sprayed to runoff with aqueoussuspensions containing (dry basis) 80% of active ingredient and 20% ofemulsifier. Two hours after the sprayed-on layer had dried, the sliceswere inoculated with a spore suspension of the fungus Botrytis cinerea,which contained 1.7×10⁶ spores per ml of a 2% strength malt solution.The inoculated slices were then incubated in humid chambers at 18° C.for 4 days. The development of Botrytis on the slices attacked was thenassessed visually.

The results show that active ingredients 1.5, 1.7 and 1.8, applied assprayliquors containing 500 ppm of active ingredient, have a betterfungicidal action (95%) than prior art comparative compounds A (10%) andB (65%).

Use Example 2 Action on Botrytis cinerea in paprika

Paprika pods were slit open and the inside surfaces were sprayed torunoff with aqueous active ingredient formulations containing (drybasis) 80% of active ingredient and 20% of emulsifier. After thesprayed-on layer had dried, the pieces were inoculated with an aqueoussuspension containing 1.7×10⁶ spores of Botrytis cinerea per ml.

The paprika pieces were then kept for 4 days in climatic cabinets at20°-2° C. The extent of fungus spread was then assessed visually.

The results show that compounds 2.4, 4.4, 6.4, 7.4, 7.5, 9.1, 9.2, 9.4,9.5, 10.1, 10.2, 10.4, 10.5, 12.4, 12.6, 2.65 and 2.66, applied asaqueousspray liquors containing 1,000 ppm of active ingredient, have agood fungicidal action (100%).

We claim:
 1. A method for treating Botrytis infestation comprisingapplying to a subject in need thereof, an effective amount of a compoundof formula ##STR36## where A has the following meanings:pyridin-3-ylsubstituted in the 2-position by halogen, methyl, trifluoromethyl,methoxy, methylthio, methylsulfinyl or methylsulfonyl, R has thefollowing meanings: unsubstituted or halogen-substituted C₂ -C₁₂ -alkyl,unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl,unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted orhalogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy,unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl,unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl,unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy,unsubstituted or C₁ -C₄ -alkyl substituted C₅ -C₆ -cycloalkenyloxy, orphenyl which is unsubstituted or substituted by C₁ -C₄ -alkyl, C₁ -C₄-alkoxy, C₁ -C₄ -alkylthio or halogen, with the proviso that when R isunsubstituted phenyl, A cannot be 2-chloropyridine-3-yl, in a suitablecarrier.
 2. A method for treating Botrytis infestation comprisingadministering to a subject in need thereof an effective amount of acompound of formula I ##STR37## where the substituents have thefollowing meanings: R¹ is halogen, methyl, trifluoromethyl, methoxy,methylthio, methylsulfinyl, or methylsulfonylR² is unsubstituted orhalogen-substituted C₂ -C₁₂ -alkyl, unsubstituted or halogen-substitutedC₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substitutedC₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂-alkenyloxy, C₃ -C₁₂ -alkynyloxy, C₃ -C₆ -cycloalkyl, C₄ -C₆-cycloalkenyl, C₅ -C₆ -cycloalkyloxy, or C₅ -C₆ -cycloalkenyloxy, in asuitable carrier.
 3. A method for treating Botrytis infestationcomprising administering to a subject in need thereof an effectiveamount of a compound of formula III ##STR38## where the substituentshave the following meanings: A is ##STR39## X is methylene, sulfur,sulfinyl, or sulfonyl (SO₂) R¹ is methyl, trifluoromethyl, chlorine,bromine or iodineR² is trifluoromethyl or chlorine R³ is hydrogen ormethyl R⁴ is methyl, trifluoromethyl or chlorine R⁵ is hydrogen, methylor chlorine R⁶ is methyl or trifluoromethyl R⁷ is methyl or chlorine R⁸is C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or halogen, in asuitable carrier.
 4. A method for treating Botrytis infestationcomprising administering to a subject in need thereof an effectiveamount of a compound of formula IV, ##STR40## where the substituentshave the following meanings: A isX is methylene, sulfonyl or sulfonyl(SO₂) R¹ is methyl, trifluoromethyl, chlorine, bromine or iodine R² istrifluoromethyl R³ is hydrogen or methyl R⁴ is methyl, trifluoromethylor chlorine R⁵ is hydrogen, methyl or chlorine R⁶ is methyl ortrifluoromethyl R⁷ is methyl or chlorine,in a suitable carrier.